Ortho-substituted 2-methoxyiminophenyl-N-methylacetamides

ABSTRACT

Compounds of the general formula I ##STR1## where the index and the substituents have the following meanings: n is 0 or 1 to 4; 
     X is O or S; 
     Y is a five-membered heteroaromatic ring; 
     R 1  is nitro; cyano; halogen; alkyl; haloalkyl; alkoxy; haloalkoxy; alkylthio; phenyl or phenoxy; 
     R 2  is hydrogen; alkyl, alkenyl or alkynyl; 
     or a saturated or unsaturated ring which, in addition to carbon atoms, can also contain hetero atoms as ring members are described.

The present invention relates to compounds of the general formula##STR2## where the index and the substituents have the followingmeanings: n is 0, 1, 2, 3 or 4, it being possible for the radicals R¹ tobe different if n is greater than 1;

X is O or S;

Y is a five-membered heteroaromatic ring which, in addition to R², canalso carry one or two radicals from the group consisting of Cl, CH₃, CF₃and OCH₃ ;

R¹ is nitro; cyano; halogen;

C₁ -C₄ -alkyl; C₁ -C₄ -haloalkyl; C₁ -C₄ -alkoxy; C₁ -C₄ -haloalkoxy; C₁-C₄ -alkylthio;

phenyl or phenoxy, it being possible for the aromatic rings to carry oneto five halogen atoms or one to three of the following radicals:halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₄-haloalkoxy and C₁ -C₄ -alkylthio;

or, if n is greater than 1, a 1,3-butadiene-1,4-diyl group which isbonded to two adjacent C atoms of the phenyl radical and which for itspart can carry one to four halogen atoms or one or two of the followingradicals: nitro, cyano, halogen, C₁ -C₄ -alkyl, C₁ -C₄ -haloalkyl, C₁-C₄ -alkoxy, C₁ -C₄ -haloalkoxy and C₁ -C₄ -alkylthio;

R² is hydrogen;

unsubstituted or substituted alkyl, alkenyl or alkynyl;

an unsubstituted or substituted, saturated or mono- or diunsaturatedring which, in addition to carbon atoms, can contain one to three of thefollowing hetero atoms as ring members: oxygen, sulfur and nitrogen;

or an unsubstituted or substituted, mono- or binuclear aromatic ringwhich, in addition to carbon atoms, can contain one to four nitrogenatoms or one or two nitrogen atoms and an oxygen or sulfur atom or anoxygen or sulfur atom as ring members.

The invention further relates to processes for preparing thesecompounds, compositions containing them and their use for the control offungi and pests.

Substituted 2-alkoxyiminophenylacetamides are known (EP-A 398 692, EP-A477 631, JP-A 4 182 461, WO 92/13 830 and GB 22 53 624). The compoundshave fungicidal and partly also insecticidal action (EP-A 477 631).Their action, however, is unsatisfactory.

It has surprisingly been found that the compounds of the general formulaI according to the invention have a greatly improved activity and planttolerability.

In addition, processes for preparing these compounds, compositionscontaining them and their use for the control of fungi and pests havebeen found.

The compounds of the formula I are prepared in analogy to variousmethods known per se from the literature. In the synthesis of thecompounds I, the sequence in which the groups R² --Y--XCH₂ -- or group[sic] --C(═NOCH₃)--CO--NHCH₃ are synthesized from the correspondingprecursors is in general insignificant.

These groups are particularly preferably obtained by the processesdescribed below, the group which is not involved in the reaction in eachcase being shown in the following reaction schemes in a simplifiedmanner for better clarity:

the group R² --Y--XCH₂ -- or its precursor as R* and the group--C(═NOCH₃)--CO--NHCH₃ or its precursor as R^(#).

A: Process for Synthesizing the Group R² --Y--XCH₂ --

The compounds of the general formulae I and II are obtained by reactionof IA or IIA with hydroxy- or mercapto-substituted five-membered ringheteroaromatic systems III in inert solvents in the presence of a base.##STR3##

This reaction is customarily carried out at from 0° C. to 80° C.,preferably 20° C. to 60° C. Suitable solvents are aromatic hydrocarbonssuch as toluene, o-, m- and p-xylene, halogenated hydrocarbons such asdichloromethane, chloroform and chlorobenzene, ethers such as diethylether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole andtetrahydrofuran, nitrites such as acetonitrile and propionitrile,alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, ketones such as acetone and methyl ethyl ketone, aswell as dimethyl sulfoxide, dimethylformamide, dimethylacetamide,1,3-dimethylimidazolidin-2-one and1,3-dimethyltetrahydro-2(1H)-pyrimidinine [sic], particularly preferablydichloromethane, acetone and dimethylformamide.

Mixtures of the solvents mentioned can also be used.

Suitable bases are generally inorganic compounds such as alkali metaland alkaline earth metal hydroxides such as lithium hydroxide, sodiumhydroxide, potassium hydroxide, calcium hydroxide, alkali metal andalkaline earth metal oxides such as lithium oxide, sodium oxide, calciumoxide and magnesium oxide, alkali metal and alkaline earth metalhydrides such as lithium hydride, sodium hydride, potassium hydride andcalcium hydride, alkali metal amides such as lithium amide, sodium amideand potassium amide, alkali metal and alkaline earth metal carbonatessuch as potassium carbonates [sic] and calcium carbonate and also alkalimetal hydrogen carbonates such as potassium carbonate and calciumcarbonate [sic] and also alkali metal hydrogen carbonates such as sodiumhydrogen carbonate, organometallic compounds, in particular alkali metalalkyls such as methyllithium, butyllithium and phenyllithium,alkymagnesium [sic] halides such as methylmagnesium chloride and alsoalkali metal and alkaline earth metal alkoxides such as sodiummethoxide, sodium methoxide [sic], potassium ethoxide, potassiumtert-butoxide and dimethoxymagnesium and additionally organic bases, eg.tertiary amines such as trimethylamine, triethylamine,diisopropylethylamine and N-methylpiperidine, pyridine, substitutedpyridines such as collidine, lutidine and 4-dimethylaminopyridine andalso bicyclic amines.

Sodium hydroxide, sodium hydride, potassium carbonate and potassiumtert-butoxide are particularly preferred.

The bases are in general used in equimolar amounts, in an excess or ifappropriate as a solvent.

It may be advantageous for the reaction to add a catalytic amount of acrown ether such as eg. 18-crown-6 or 15-crown-5.

The reaction can also be carried out in a two-phase system consist [sic]of a solution of alkali metal or alkaline earth metal hydroxides oralkali metal or alkaline earth metal carbonates in water and an organicphase such as eg. halogenated hydrocarbons. Phase-transfer catalystsemployed can be ammonium halides and tetrafluoborates such as eg.benzyltriethylammonium chloride, benzyltributylammonium bromide,tetrabutylammonium chloride, hexadecyltrimethylammonium bromide ortetrabutylammonium tetrafluoborate and also phosphonium halides such astetrabutylphosphonium chloride or tetraphenylphosphonium bromide.

It may be advantageous for the reaction first to treat the compounds IIIwith base and to react the resulting salt with the compounds IA or IIA.

The starting compounds IA.1 (L=Cl) and IA.2 (L=Br), cf. EP477631, Tab.1, No. 332 and 333, are prepared from corresponding alkoxy or aryloxycompounds IB by cleavage ##STR4## with eg. boron trichloride (for IA.1)or with hydrogen bromide (for IA.2) in inert solvents such ashalogenated hydrocarbons at from -30° C. to +40° C. An advantageouspreparation from R'=2-tolyl (see EP-A477631, Tab. 1, No. 94) isdescribed in Examples 1 to 3.

The preparation of the starting compounds IIA is described several timesin the literature, cf. EP-A 363 818.

The preparation of the hydroxy- or mercapto-[lacuna] five-membered ringheterocycles III is described in the literature, or can be carried outanalogously to the synthesis routes shown there, cf. J. Heterocycl.Chem. 19 (1982), 541 ff; Acta Chem. Scand. 7 (1953), 374 ff; Chem.Pharm. Bull. 33 (1985), 3479 ff; Acta Chem. Scand. 17 (1963), 144ff;Canadian Patent 1 177 081; Can J. Chem. 57 (1979), 904 ff; Ann. Chem.338 (1905), 273 ff; German Laid-Open Application DOS 1029827; Chem.Pharm. Bull. 15 (1967), 1025 ff; Agric. Biol. Chem. 50 (1986), 1831 ff;J. Org. Chem. 23 (1958), 1021 ff; Chem. Ber. 22 (1889), 2433 ff; Chem.Ber. 24 (1891), 369 ff; J. Med. Chem. 15 (1971), 39 ff; J. Am. Chem.Soc. 76 (1954), 4450 ff.

B: Process for Synthesizing the Group --C(═NOCH₃)--CO--NHCH₃

The compounds of the general formula I are obtained by aminolysis of thecorresponding 2-methoxyiminophenylacetic acid esters II (cf. Houben-WeylVol. E 5, p. 983 ff). ##STR5##

This reaction is customarily carried out at from 0° C. to 60° C;,preferably 10° C. to 30° C.

Methylamine can be metered into a solution of II by gaseous introductionor as an aqueous solution.

Suitable solvents are aromatic hydrocarbons such as toluene, o-, m- andp-xylene, halogenated hydrocarbons such as dichloromethane, chloroformand chlorobenzene, ethers such as diethyl ether, diisopropyl ether,tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, andalcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanoland tert-butanol, particularly preferably methanol, toluene andtetrahydrofuran.

Mixtures of the solvents mentioned can also be used.

With respect to the biological action against pests such as inparticular harmful fungi, insects, nematodes and arachnida, thosecompounds I are particularly suitable in which the index and thesubstituents have the following meanings:

n is 0, 1, 2, 3 or 4, it being possible for the radicals R¹ to bedifferent if n is greater than 1, in particular 0 or 1;

X is O or S;

Y is a five-membered ring heteroaromatic system such as 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,2,4-triazol-5-yl,1,3,4-oxadiazol-2-yl, 1,3,4-thiadiazol-2-yl, 1,2,3-oxadiazol-4-yl,1,2,3-oxadiazol-5-yl, 1,2,3-triazol-5-yl and 1,2,3-triazol-4-yl, inparticular 2-furyl, 2-thienyl, 3-pyrrolyl, 3-isoxazolyl, 5-isoxazolyl,3-isothiazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl,4-oxazolyl, 2-thiazolyl, 4-thiazolyl, 1,2,4-oxadiazol-5-yl,1,2,4-thiadiazol-5-yl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl and1,3,4-thiadiazol-2-yl;

R¹ is nitro;

cyano;

halogen such as fluorine, chlorine, bromine and iodine, in particularfluorine and chlorine;

C₁ -C₄ -alkyl such as methyl, ethyl, propyl, 1-methylethyl, butyl,1-methylpropyl, 2-methylpropyl and 1,1-dimethylethyl, preferably methyland 1-methylethyl, in particular methyl;

C₁ -C₄ -haloalkyl, particularly C₁ -C₂ -haloalkyl such astrichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl,1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl,2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl,2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl,preferably difluoromethyl and trifluoromethyl, in particulartrifluoromethyl;

C₁ -C₄ -alkoxy such as methoxy, ethoxy, propyloxy, 1-methylethoxy,butyloxy, 1-methylpropyloxy, 2-methylpropyloxy and 1,1-dimethylethoxy,preferably methoxy and ethoxy, 1-methylethoxy, in particular methoxy;

C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy such asdichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy,trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy,chlorodifluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy,2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy,2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy,2,2,2-trichloroethoxy and pentafluoroethoxy, preferably difluoromethoxyand chlorodifluoromethoxy, in particular difluoromethoxyoxy [sic];

C₁ -C₄ -alkylthio such as methylthio, ethylthio, propylthio,1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and1,1-dimethylethylthio, preferably methylthio, ethylthio and1-methylethylthio, in particular methylthio;

phenyl or phenoxy, where the aromatic rings can carry one to fivehalogen atoms such as fluorine, chlorine, bromine and iodine, inparticular fluorine and chlorine or one to three of the followingradicals:

halogen such as mentioned above;

C₁ -C₄ -alkyl such as mentioned above, in particular methyl;

C₁ -C₄ -haloalkyl, particularly C₁ -C₂ -haloalkyl such as mentionedabove, in particular trifluoromethyl;

C₁ -C₄ -alkoxy such as mentioned above, in particular methoxy;

or, if n>1, a 1,3-butadiene-1,4-diyl group which is bonded to twoadjacent C atoms of the parent structure and which for its part cancarry one to four halogen atoms such as fluorine, chlorine, bromine andiodine, in particular fluorine and chlorine, or one or two of thefollowing radicals:

halogen such as mentioned above,

nitro,

cyano,

C₁ -C₄ -alkyl such as mentioned above, in particular methyl;

C₁ -C₄ -haloalkyl, particularly C₁ -C₂ -haloalkyl such as mentionedabove, in particular trifluoromethyl;

C₁ -C₄ -alkoxy such as mentioned above, in particular methoxy;

R² is unsubstituted or substituted alkyl, in particular C₁ -C₆ -alkylsuch as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl,2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl,3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl,1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl,3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl,1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl,3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl,1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and1-ethyl-2-methylpropyl, preferably methyl, ethyl, 1-methylethyl,1-methylpropyl, 1,1-dimethylethyl, 1,1-dimethylpropyl and2,3-dimethylbutyl, in particular methyl, 1-methylethyl and1,1-dimethylethyl;

unsubstituted or substituted alkenyl, particularly C₂ -C₆ -alkenyl suchas ethenyl, 2-propenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl,2-methyl-2-propenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl,1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl,1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl,1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-2-propenyl,2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-2-pentenyl,2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl,1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl,4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl,1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl,1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl,2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-2-butenyl,1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-2-butenyl,2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl,1-ethyl-1-methyl-2-propenyl and 1-ethyl-2-methyl-2-propenyl, preferably1-propenyl, 1-methyl-2-propenyl, 1,1-dimethyl-2-propenyl,1,1-dimethyl-2-butenyl, in particular 2-propenyl and1,1-dimethyl-2-propenyl;

or unsubstituted or substituted alkynyl, particularly C₃ -C₆ -alkynylsuch as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl,2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl,1-methyl-3-butynyl, 2-methyl-3-butynyl, 1,1-dimethyl-2-propynyl,1-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl,1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl,2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl,4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl,1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl,1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and1-ethyl-1-methyl-2-propynyl, preferably 2-propynyl, 1-methyl-2-propynyl,1-methyl-2-butynyl, 1,1-dimethyl-2-propynyl and 1,1-dimethyl-2-butynyl,in particular 2-propynyl, 1-methyl-2-propynyl and1,1-dimethyl-2-propynyl;

an unsubstituted or substituted, saturated or mono- or diunsaturatedring which, in addition to carbon atoms, can contain one to three of thefollowing hetero atoms as ring members: oxygen, sulfur and nitrogen, forexample carbocycles such as cyclopropyl, cyclopentyl, cyclohexyl,cyclopent-2-enyl, cyclohex-2-enyl, 5- to 6-membered, saturated orunsaturated heterocycles, containing one to three nitrogen atoms and/oran oxygen or sulfur atom such as 2-tetrahydrofuranyl,3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl,2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, 4-isoxazolidinyl,5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl,5-isothiazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl,2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl,4-thiazolidinyl, 5-thiazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl,1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl,1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl,1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl,1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl,2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl,2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl,2,4-dihydrothien-3-yl, 2,3-pyrrolin-2-yl, 2,3-pyrrolin-3-yl,2,4-pyrrolin-2-yl, 2,4-pyrrolin-3-yl, 2,3-isoxazolin-3-yl,3,4-isoxazolin-3-yl, 4,5-isoxazolin-3-yl, 2,3-isoxazolin-4-yl,3,4-isoxazolin-4-yl, 4,5-isoxazolin-4-yl, 2,3-isoxazolin-5-yl,3,4-isoxazolin-5-yl, 4,5-isoxazolin-5-yl, 2,3-isothiazolin-3-yl,3,4-isothiazolin-3-yl, 4,5-isothiazolin-3-yl, 2,3-isothiazolin-4-yl,3,4-isothiazolin-4-yl, 4,5-isothiazolin-4-yl, 2,3-isothiazolin-5-yl,3,4-isothiazolin-5-yl, 4,5-isothiazolin-5-yl, 2,3-dihydropyrazol-1-yl,2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl,2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl,3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl,3,4-dihydropyrazol-4-yl, 3,4-dihydropyrazol-5-yl,4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl,4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl,2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl,2,3-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl,3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl,3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 2-piperidinyl,3-piperidinyl, 4-piperidinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl,4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-tetrahydropyridazinyl,4-tetrahydropyridazinyl, 2-tetrahydropyrimidinyl,4-tetrahydropyrimidinyl, 5-tetrahydropyrimidinyl, 2-tetrahydropyrazinyl,1,3,5-tetrahydrotriazin-2-yl and 1,2,4-tetrahydrotriazin-3-yl,preferably 2-tetrahydrofuranyl, 2-tetrahydrothienyl, 2-pyrrolidinyl,3-isoxazolidinyl, 3-isothiazolidinyl, 1,3,4-oxazolidin-2-yl,2,3-dihydrothien-2-yl, 4,5-isoxazolin-3-yl, 3-piperidinyl,1,3-dioxan-5-yl, 4-piperidinyl, 2-tetrahydropyranyl,4-tetrahydropyranyl;

or an unsubstituted or substituted mono- or binuclear aromatic ringsystem which, in addition to carbon atoms, can contain one to fournitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atomor an oxygen or sulfur atom as ring members, ie. aryl radicals such asphenyl and naphthyl, preferably phenyl or 1- or 2-naphthyl, and hetarylradicals, for example 5-membered ring heteroaromatics containing one tothree nitrogen atoms and/or an oxygen or sulfur atom such as 2-furyl,3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl,3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl,4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl,5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 1-imidazolyl, 2-imidazolyl, 4-imidazolyl,1,2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, 1,2,4-thiadiazol-3-yl,1,2,4-thiadiazol-5-yl, 1,2,5-triazol-3-yl, 1,2,3-triazol-4-yl,1,2,3-triazol-5-yl, 1,2,3-triazol-4-yl, 5-tetrazolyl,1,2,3,4-thiatriazol-5-yl and 1,2,3,4-oxatriazol-5-yl, in particular3-isoxazolyl, 5-isoxazolyl, 4-oxazolyl, 4-thiazolyl,1,3,4-oxadiazol-2-yl and 1,3,4-thiadiazol-2-yl;

six-membered ring heteroaromatics containing one to four nitrogen atomsas hetero atoms such as 2-pyridinyl, 3-pyridinyl, 4-pyridinyl,3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl,5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and1,2,4,5-tetrazin-3-yl, in particular 2-pyridinyl, 3-pyridinyl,4-pyridinyl, 2-pyrimidinyl, 4-pyrimidinyl, 2-pyrazinyl and4-pyridazinyl.

The mono- or binuclear aromatic or heteroaromatic systems mentionedunder the radicals can for their part be partially or completelyhalogenated, ie. the hydrogen atoms of these groups can be replacedpartially or completely by halogen atoms such as fluorine, chlorine,bromine and iodine, preferably fluorine and chlorine.

In addition to the designated halogen atoms, these mono- or bi-nucleararomatic or heteroaromatic systems can additionally carry one to threeof the following substituents:

nitro;

cyano, thiocyanato;

alkyl, particularly C₁ -C₆ -alkyl such as mentioned above, preferablymethyl, ethyl, 1-methylethyl, 1,1-dimethylethyl, butyl, hexyl, inparticular methyl and 1-methylethyl;

alkenyl, particularly preferably C₂ -C₆ -alkenyl such as mentionedabove, preferably ethenyl, 1-propenyl, 2-propenyl, 1-methyl-2-propenyl,2-butenyl, 3-butenyl, 3-hexenyl, in particular ethenyl, 2-propenyl and2-butenyl;

alkynyl, particularly C₂ -C₆ -alkynyl such as mentioned above,preferably ethynyl, 2-propynyl, 1-methyl-2-butynyl,1,1-dimethyl-2-butynyl, in particular ethynyl and1,1-dimethyl-2-butynyl;

C₁ -C₄ -haloalkyl such as mentioned above, preferably trichloromethyl,difluoromethyl, trifluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyland pentafluoroethyl;

C₁ -C₄ -alkoxy, preferably methoxy, ethoxy, 1-methylethoxy and1,1-dimethylethoxy, in particular methoxy;

C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy, preferablydifluoromethoxy, trifluoromethoxy and 2,2,2-trifluoroethoxy, inparticular difluoromethoxy;

C₁ -C₄ -alkylthio, preferably methylthio and 1-methylethylthio, inparticular methylthio;

C₁ -C₄ -alkylamino such as methylamino, ethylamino, propylamino,1-methylethylamino, butylamino, 1-methylpropylamino, 2-methylpropylaminoand 1,1-dimethylethylamino, preferably methylamino and1,1-dimethylethylamino, in particular methylamino;

di-C₁ -C₄ -alkylamino such as N,N-dimethylamino, N,N-diethylamino,N,N-dipropylamino, N,N-di-(1-methylethyl)amino, N,N-dibutylamino,N,N-di-(1-methylpropyl)amino, N,N-di-(2-methylpropyl)amino,N,N-di-(1,1-dimethylethyl)amino, N-ethyl-N-methylamino,N-methyl-N-propylamino, N-methyl-N-(1-methylethyl)amino,N-butyl-N-methylamino, N-methyl-N-(1-methylpropyl)amino,N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino,N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino,N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino,N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(1,1-dimethylethyl)amino,N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino,N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino,N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino,N-(1-methylethyl)-N-(1-methylpropyl)amino,N-(1-methylethyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylethyl)amino,N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino,N-butyl-N-(1,1-dimethylethyl)amino,N-(1-methylpropyl)-N-(2-methylpropyl)amino,N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino andN-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferablyN,N-dimethylamino and N,N-diethylamino, in particular N,N-dimethylamino;

C₃ -C₆ -alkenyloxy such as 2-propenyloxy, 2-butenyloxy, 3-butenyloxy,1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyloxy,3-pentenyloxy, 4-pentenyloxy, 1-methyl-2-butenyloxy,2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy,2-methyl-3-butenyloxy, 3-methyl-3-butenyloxy,1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-2-propenyloxy,1-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy,5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy,3-methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy,2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy,1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy,4-methyl-4-pentenyloxy, 1,1-dimethyl-2-butenyloxy,1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-2-butenyloxy,1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-2-butenyloxy,1,3-dimethyl-3-butenyloxy, 2,2-dimethyl-3-butenyloxy,2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy,3,3-dimethyl-2-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy,2-ethyl-2-butenyloxy, 2-ethyl-3-butenyloxy,1,1,2-trimethyl-2-propenyloxy, 1-ethyl-1-methyl-2-propenyloxy and1-ethyl-2-methyl-2-propenyloxy, preferably 2-propenyloxy and3-methyl-2-butenyloxy, in particular 2-propenyloxy;

C₃ -C₆ -alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy,1-methyl-2-propynyloxy, 2-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy,1-methyl-2-butynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy,1,1-dimethyl-2-propynyloxy, 1-ethyl-2-propynyloxy, 2-hexynyloxy,3-hexynyloxy, 4-hexynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy,1-methyl-3-pentynyloxy, 1-methyl-4-pentynyloxy, 2-methyl-3-pentynyloxy,2-methyl-4-pentynyloxy, 3-methyl-4-pentynyloxy, 4-methyl-2-pentynyloxy,1,1-dimethyl-2-butynyloxy, 1,1-dimethyl-3-butynyloxy,1,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3-butynyloxy,1-ethyl-2-butynyloxy, 1-ethyl-3-butynyloxy, 2-ethyl-3-butynyloxy and1-ethyl-1-methyl-2-propynyloxy, preferably 2-propynyloxy and2-butynyloxy, in particular 2-propynyloxy;

C₁ -C₆ -alkylcarbonyl such as methylcarbonyl, ethylcarbonyl,propylcarbonyl, 1-methylethylcarbonyl, butylcarbonyl,1-methylpropylcarbonyl, 2-methylpropylcarbonyl,1,1-dimethylethylcarbonyl, pentylcarbonyl, 1-methylbutylcarbonyl,2-methylbutylcarbonyl, 3-methylbutylcarbonyl,1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl,2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, hexylcarbonyl,1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl,4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl,1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl,2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl,3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl,1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl,1-ethyl-1-methylpropylcarbonyl and 1-ethyl-2-methylpropylcarbonyl,preferably methylcarbonyl, ethylcarbonyl and 1,1-dimethylcarbonyl, inparticular ethylcarbonyl;

C₁ -C₆ -alkoxycarbonyl such as methoxycarbonyl, ethoxycarbonyl,propyloxycarbonyl, 1-methylethoxycarbonyl, butyloxycarbonyl,1-methylpropyloxycarbonyl, 2-methylpropyloxycarbonyl,1,1-dimethylethoxycarbonyl, pentyloxycarbonyl, 1-methylbutyloxycarbonyl,2-methylbutyloxycarbonyl, 3-methylbutyloxycarbonyl,2,2-dimethylpropyloxycarbonyl, 1-ethylpropyloxycarbonyl,hexyloxycarbonyl, 1,1-dimethylpropoxycarbonyl,1,2-dimethylpropyloxycarbonyl, 1-methylpentyloxycarbonyl,2-methylpentyloxycarbonyl, 3-methylpentyloxycarbonyl,4-methylpentyloxycarbonyl, 1,1-dimethylbutyloxycarbonyl,1,2-dimethylbutyloxycarbonyl, 1,3-dimethylbutyloxycarbonyl,2,2-dimethylbutyloxycarbonyl, 2,3-dimethylbutyloxycarbonyl,3,3-dimethylbutyloxycarbonyl, 1-ethylbutyloxycarbonyl,2-ethylbutyloxycarbonyl, 1,1,2-trimethylpropyloxycarbonyl,1,2,2-trimethylpropyloxycarbonyl, 1-ethyl-1-methylpropyloxycarbonyl and1-ethyl-2-methylpropyloxycarbonyl, preferably methoxycarbonyl,ethoxycarbonyl and 1,1-dimethylethoxycarbonyl, in particularethoxycarbonyl;

C₁ -C₆ -alkylthiocarbonyl such as methylthiocarbonyl, ethylthiocarbonyl,propylthiocarbonyl, 1-methylethylthiocarbonyl, butylthiocarbonyl,1-methylpropylthiocarbonyl, 2-methylpropylthiocarbonyl,1,1-dimethylethylthiocarbonyl, pentylthiocarbonyl,1-methylbutylthiocarbonyl, 2-methylbutylthiocarbonyl,3-methylbutylthiocarbonyl, 2,2-dimethylpropylthiocarbonyl,1-ethylpropylthiocarbonyl, hexylthiocarbonyl,1,1-dimethylpropthiocarbonyl [sic], 1,2-dimethylpropylthiocarbonyl,1-methylpentylthiocarbonyl, 2-methylpentylthiocarbonyl,3-methylpentylthiocarbonyl, 4-methylpentylthiocarbonyl,1,1-dimethylbutylthiocarbonyl, 1,2-dimethylbutylthiocarbonyl,1,3-dimethylbutylthiocarbonyl, 2,2-dimethylbutylthiocarbonyl,2,3-dimethylbutylthiocarbonyl, 3,3-dimethylbutylthiocarbonyl,1-ethylbutylthiocarbonyl, 2-ethylbutylthiocarbonyl,1,1,2-trimethylpropylthiocarbonyl, 1,2,2-trimethylpropylthiocarbonyl,1-ethyl-1-methylpropylthiocarbonyl and1-ethyl-2-methylpropylthiocarbonyl, preferably methylthiocarbonyl and1-methylethylthiocarbonyl, in particular methylthiocarbonyl;

C₁ -C₆ -alkylaminocarbonyl such as methylaminocarbonyl,ethylaminocarbonyl, propylaminocarbonyl, 1-methylethylaminocarbonyl,butylaminocarbonyl, 1-methylpropylaminocarbonyl,2-methylpropylaminocarbonyl, 1,1-dimethylethylaminocarbonyl,pentylaminocarbonyl, 1-methylbutylaminocarbonyl,2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl,2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl,hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl,1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl,2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl,4-methylpentylaminocarbonyl, 1,1,-dimethylbutylaminocarbonyl,1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl,2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl,3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl,2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl,1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyland 1-ethyl-2-methylpropylaminocarbonyl, preferably methylaminecarbonyl[sic] and ethylaminecarbonyl [sic], in particular methylaminocarbonyl;

di-C₁ -C₆ -alkylaminocarbonyl, particularly di-C₁ -C₄-alkylaminocarbonyl such as N,N-dimethylaminocarbonyl,N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl,N,N-di-(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl,N,N-di-(1-methylpropyl)aminocarbonyl,N,N-di-(2-methylpropyl)aminocarbonyl,N,N-di-(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl,N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl,N-methyl-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-methylaminocarbonyl,N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl,N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl,N-ethyl-N-(2-methylpropyl)aminocarbonyl,N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl,N-(1-methylpropyl)-N-propylaminocarbonyl,N-(2-methylpropyl)-N-propylaminocarbonyl,N-(1,1-dimethylethyl)-N-propylaminocarbonyl,N-butyl-N-(1-methylethyl)aminocarbonyl,N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl,N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl,N-butyl-N-(1-methylpropyl)aminocarbonyl,N-butyl-N-(2-methylpropyl)aminocarbonyl,N-butyl-N-(1,1-dimethylethyl)aminocarbonyl,N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl,N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl andN-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, preferablyN,N-dimethylaminocarbonyl and N,N-diethylaminocarbonyl, in particularN,N-dimethylaminocarbonyl;

C₁ -C₆ -alkylcarboxyl such as methylcarboxyl, ethylcarboxyl,propylcarboxyl, 1-methylethylcarboxyl, butylcarboxyl,1-methylpropylcarboxyl, 2-methylpropylcarboxyl,1,1-dimethylethylcarboxyl, pentylcarboxyl, 1-methylbutylcarboxyl,2-methylbutylcarboxyl, 3-methylbutylcarboxyl,1,1-dimethylpropylcarboxyl, 1,2-dimethylpropylcarboxyl,2,2-dimethylpropylcarboxyl, 1-ethylpropylcarboxyl, hexylcarboxyl,1-methylpentylcarboxyl, 2-methylpentylcarboxyl, 3-methylpentylcarboxyl,4-methylpentylcarboxyl, 1,1-dimethylbutylcarboxyl,1,2-dimethylbutylcarboxyl, 1,3-dimethylbutylcarboxyl,2,2-dimethylbutylcarboxyl, 2,3-dimethylbutylcarboxyl,3,3-dimethylbutylcarboxyl, 1-ethylbutylcarboxyl, 2-ethylbutylcarboxyl,1,1,2-trimethylpropylcarboxyl, 1,2,2-trimethylpropylcarboxyl,1-ethyl-1-methylpropylcarboxyl and 1-ethyl-2-methylpropylcarboxyl,preferably methylcarboxyl, ethylcarboxyl and 1,1-dimethylethylcarbonyl[sic], in particular methylcarboxyl and 1,1-dimethylethylcarboxyl;

C₁ -C₆ -alkylcarbonylamino such as methylcarbonylamino,ethylcarbonylamino, propylcarbonylamino, 1-methylethylcarbonylamino,butylcarbonylamino, 1-methylpropylcarbonylamino,2-methylpropylcarbonylamino, 1,1-dimethylethylcarbonylamino,pentylcarbonylamino, 1-methylbutylcarbonylamino,2-methylbutylcarbonylamino, 3-methylbutylcarbonylamino,2,2-dimethylpropylcarbonylamino, 1-ethylpropylcarbonylamino,hexylcarbonylamino, 1,1-dimethylpropylcarbonylamino,1,2-dimethylpropylcarbonylamino, 1-methylpentylcarbonylamino,2-methylpentylcarbonylamino, 3-methylpentylcarbonylamino,4-methylpentylcarbonylamino, 1,1-dimethylbutylcarbonylamino,1,2-dimethylbutylcarbonylamino, 1,3-dimethylbutylcarbonylamino,2,2-dimethylbutylcarbonylamino, 2,3-dimethylbutylcarbonylamino,3,3-dimethylbutylcarbonylamino, 1-ethylbutylcarbonylamino,2-ethylbutylcarbonylamino, 1,1,2-trimethylpropylcarbonylamino,1,2,2-trimethylpropylcarbonylamino, 1-ethyl-1-methylpropylcarbonylaminoand 1-ethyl-2-methylpropylcarbonylamino, preferably methylcarbonylaminoand ethylcarbonylamino, in particular ethylcarbonylamino;

C₃ -C₇ -cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl and cycloheptyl, preferably cyclopropyl, cyclopentyl andcyclohexyl, in particular cyclopropyl;

C₃ -C₇ -cycloalkoxy such as cyclopropyloxy, cyclobutyloxy,cyclopentyloxy, cyclohexyloxy and cycloheptyloxy, preferablycyclopentyloxy and cyclohexyloxy, in particular cyclohexyloxy;

C₃ -C₇ -cycloalkylthio such as cyclopropylthio, cyclobutylthio,cyclopentylthio, cyclohexylthio and cycloheptylthio, preferablycyclohexylthio;

C₃ -C₇ -cycloalkylamino such as cyclopropylamino, cyclobutylamino,cyclopentylamino, cyclohexylamino and cycloheptylamino, preferablycyclopropylamino and cyclohexylamino, in particular cyclopropylamino;

C₅ -C₇ -cycloalkenyl such as cyclopenten-1-yl, cyclopenten-2-yl,cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-2-yl, cyclohexen-3-yl,cyclohepten-1-yl, cyclohepten-2-yl, cyclohepten-3-yl andcyclohepten-4-yl, preferably cyclopenten-1-yl, cyclopenten-3-yl andcyclohexen-2-yl, in particular cyclopenten-1-yl;

5- to 6-membered, saturated or unsaturated heterocycles containing oneto three nitrogen atoms and/or an oxygen or sulfur atom such asmentioned above, preferably tetrahydropyrazin-1-yl and2-tetrahydrofuranyl, tetrahydropyran-4-yl and 1,3-dioxan-2-yl;

phenyl;

5-membered ring heteroaromatics containing one to three nitrogen atomsand/or an oxygen or sulfur atom such as mentioned above, preferably3-furyl, 3-thienyl, 5-isoxazolyl, 3-isoxazolyl, 4-oxazolyl,1,3,4-thiadiazol-3-yl and 2-thienyl,

it being possible for a benzene ring to be fused to the abovementioned5-membered heteroaromatic;

6-membered ring heteroaromatics containing one to three nitrogen atomsas hetero atoms, preferably 5-pyrimidyl and 3-pyridinyl, it beingpossible for the abovementioned aryl and heteroaryl rings to carry oneto three of the following groups: fluorine, chlorine, cyano, methyl,methoxy, trifluoromethyl and trifluoromethoxy.

Two adjacent radicals R² can have the meaning of an oxy-C₁ -C₂-alkylidenoxy chain which is unsubstituted or substituted by flurine[sic], such as eg. --O--CH₂ --O, --O--CF₂ --O--, --O--CH₂ CH₂ --O-- or--O--CF₂ CF₂ --O--, or of a C₃ -C₄ -alkylidene chain, such as eg.propylidene or butylidene.

The alkyl, alkenyl and alkynyl groups mentioned under the radical R² canfor their part be partially or completely halogenated, ie. the hydrogenatoms of these groups can be partially or completely replaced by halogenatoms such as fluorine, chlorine, bromine and iodine, preferablyfluorine and chlorine.

In addition to the designated halogen atoms, the said alkyl, alkenyl andalkynyl groups can additionally carry one to three of the followingsubstituents:

nitro;

cyano; thicyanato [sic];

C₁ -C₄ -alkoxy, preferably methoxy, ethoxy and 1-methylethoxy, inparticular methoxy;

C₁ -C₄ -haloalkoxy, particularly C₁ -C₂ -haloalkoxy, in particulardifluoromethoxy;

C₁ -C₄ -alkylthio, preferably methylthio and 1,1-dimethylethylthio, inparticular methylthio;

C₁ -C₄ -alkylamino;

di-C₁ -C₄ -alkylamino;

C₃ -C₆ -alkenyloxy, in particular 2-propenyloxy;

C₃ -C₆ -alkynyloxy, in particular 2-propynyloxy;

C₁ -C₆ -alkylcarbonyl;

C₁ -C₆ -alkoxyimino (alkyl-O--N═) such as methoxyimino, ethoxyimino,propyloxyimino, 1-methylethoxyimino, butyloxyimino,1-methylpropyloxyimino, 2-methylpropyloxyimino, 1,1-dimethylethoxyimino,pentyloxyimino, 1-methylbutyloxyimino, 2-methylbutyloxyimino,3-methylbutyloxyimino, 2,2-dimethylpropyloxyimino,1-ethylpropyloxyimino, hexyloxyimino, 1,1-dimethylpropoxyimino,1,2-dimethylpropyloxyimino, 1-methylpentyloxyimino,2-methylpentyloxyimino, 3-methylpentyloxyimino, 4-methylpentyloxyimino,1,1-dimethylbutyloxyimino, 1,2-dimethylbutyloxyimino,1,3-dimethylbutyloxyimino, 2,2-dimethylbutyloxyimino,2,3-dimethylbutyloxyimino, 3,3-dimethylbutyloxyimino,1-ethylbutyloxyimino, 2-ethylbutyloxyimino,1,1,2-trimethylpropyloxyimino, 1,2,2-trimethylpropyloxyimino,1-ethyl-1-methylpropyloxyimino and 1-ethyl-2-methylpropyloxyimino,preferably methoxyimino, ethoxyimino, propyloximino,1,1-dimethylethyloximino and 1-methylethyloximino, in particularmethyloximino and ethyloximino;

C₃ -C₆ -alkenyloxyimino, ie. C₃ -C₆ -alkenyloxy such as mentioned above,which is bonded to the structure via --N═ (imino);

C₃ -C₆ -alkynyloxyimino, ie. C₃ -C₆ -alkynyloxy such as mentioned above,which is bonded to the structure via --N═ (imino);

C₁ -C₆ -alkoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyland 1,1-dimethylethoxycarbonyl, in particular methoxycarbonyl and1,1-dimethylethoxycarbonyl;

C₁ -C₆ -alkylthiocarbonyl, in particular methylthiocarbonyl;

C₁ -C₆ -alkylaminocarbonyl, in particular methyliminocarbonyl;

di-C₁ -C₆ -alkylaminocarbonyl, in particular N,N-dimethylaminocarbonyl;

C₁ -C₆ -alkylcarboxyl, preferably methylcarboxyl and1,1-dimethylethylcarboxyl, in particular methylcarboxyl;

C₁ -C₆ -alkylcarbonylamino, preferably methylcarbonylamino and1,1-dimethylethylcarbonylamino, in particular methylcarbonylamino;

C₃ -C₇ -cycloalkyl, preferably cyclopropyl, cyclopentyl and cyclohexyl,in particular cyclopropyl;

C₃ -C₇ -cycloalkoxy, in particular cyclohexyloxy;

C₃ -C₇ -cycloalkylthio, in particular cyclohexylthio;

C₃ -C₇ -cycloalkylamino;

C₅ -C₇ -cycloalkenyl, preferably cyclopent-1-enyl, cyclopent-2-enyl andcyclohex-2-enyl, in particular cyclopent-1-entyl [sic];

5- to 6-membered, saturated or unsaturated heterocycles containing oneto three nitrogen atoms and/or an oxygen or sulfur atom, such asmentioned above, preferably tetrahydropyran-4-yl, 2-tetrahydrofuranyland 1,3-dioxan-2-yl;

aromatic systems such as phenyl, 1-naphthyl and 2-naphthyl;

5-membered ring heteroaromatics containing one to three nitrogen atomsand/or an oxygen or sulfur atom, such as mentioned above, preferably2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 5-isoxazolyl and 4-oxazolyl, inparticular 2-furyl and 2-thienyl, it being possible for a benzene ringto be fused to the abovementioned 5-membered heteroaromatics;

6-membered ring heteroaromatics containing one to three nitrogen atomsas hetero atoms such as preferably 2-pyrimidinyl, 5-pyrimidinyl and3-pyridyl, it being possible for a benzene ring to be fused to theabovementioned 6-membered heteroaromatics.

The saturated or mono- or diunsaturated alicyclic or heterocyclicsystems mentioned under the radical R² can for their part be partiallyor completely halogenated, ie. the hydrogen atoms of these groups can bereplaced partially or completely by halogen atoms such as fluorine,chlorine, bromine and iodine, preferably fluorine and chlorine.

In addition to the designated halogen atoms, these mono- ordiunsaturated alicyclic or heterocyclic systems can additionally carryone to three of the following substituents:

nitro;

cyano;

C₁ -C₆ -alkyl, preferably methyl and ethyl, in particular methyl;

C₁ -C₄ -haloalkyl, particularly C₁ -C₂ -haloalkyl, in particulartrifluoromethyl;

C₁ -C₄ -alkoxy, in particular methoxy;

C₁ -C₄ -alkylthio;

di-C₁ -C₄ -alkylamino;

C₂ -C₆ -alkenyl, preferably ethenyl, 1-propenyl, 2-propenyl and1-methylethynyl [sic], in particular ethenyl and 1-methylethenyl;

C₂ -C₆ -alkynyl, preferably ethynyl, 2-propynyl, 1-butynyl, inparticular ethynyl;

C₁ -C₆ -alkoxycarbonyl, preferably methoxycarbonyl, ethoxycarbonyl,1-methylethoxycarbonyl and 1,1-dimethylethoxycarbonyl, in particularethoxycarbonyl;

C₁ -C₆ -alkylaminocarbonyl;

di-C₁ -C₆ -alkylaminocarbonyl;

C₁ -C₆ -alkylcarboxyl, in particular methylcarboxyl;

C₁ -C₆ -alkylcarbonylamino, in particular methylcarbonylamino and1,1-dimethylcarbonylamino;

C₃ -C₇ -cycloalkyl, preferably cyclopropyl and cyclohexyl, in particularcyclopropyl;

aromatic systems such as, in particular, phenyl.

In addition, compounds I are preferred in which R¹ is halogen, C₁ -C₄-alkyl, C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -haloalkoxy or phenyl.

Those compounds I are additionally preferred in which X is oxygen.

Of particular interest are those compounds I in which Y is 3-isoxazolyl,1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 2-oxazolyl, 2-thiazolyl,4-thiazolyl, 1,2,4-triazol-3-yl, 1,3,4-oxadiazol-2-yl,1,2,4-oxadiazol-5-yl and 1,2,4-thiadiazol-5-yl, in particular3-pyrazolyl, 4-thiazolyl and 1,2,4-triazol-3-yl.

Those compounds I are particularly preferred in which R² isunsubstituted or substituted phenyl. Suitable substituents of the phenylradical are preferably halogen, cyano, C₁ -C₄ -alkyl, C₁ -C₄ -alkoxy, C₁-C₂ -haloalkyl, C₁ -C₂ -haloalkoxy, phenyl and oxy-C₁ -C₂ -alkylidenoxy.

Likewise preferred are those compounds I in which R² is unsubstituted orsubstituted five-membered ring heteroaromatics such as eg. thiazolyl,isoxazolyl, oxazolyl or 1,2,4-oxadiazolyl. Suitable substituents of thefive-membered ring heteroaromatics are preferably halogen, cyano, C₁ -C₆-alkyl, C₁ -C₆ -alkoxy, C₁ -C₄ -haloalkyl, C₁ -C₂ -haloalkoxy andphenyl.

Likewise preferred are those compounds I in which R² is unsubstituted orsubstituted six-membered ring heteroaromatics, such as eg. pyridyl,pyrimidyl, pyridazinyl or pyrazinyl. Suitable substituents of thesix-membered ring heteroaromatics are preferably halogen, cyano, C₁ -C₄-alkyl, C₁ -C₄ -alkoxy, C₁ -C₂ -haloalkyl, C₁ -C₂ -haloalkoxy andphenyl.

Likewise preferred are those compounds I in which R² is C₁ -C₆-alkoxyimino-, C₃ -C₆ -alkenyloxyimino- or C₃ -C₆-alkynyloxyimino-substituted alkyl, such as eg. methoxyiminoethyl,ethoxyiminoethyl, propoxyiminoethyl, i-propoxyiminoethyl,(2-propen)oxyiminoethyl, (2-butene)oxyiminoethyl,(2-propyn)oxyiminoethyl, methoxyiminopropyl, ethoxyiminopropyl,propoxyiminopropyl, (2-propen)oxyiminopropyl or(2-propyn)oxyiminopropyl.

Compounds of the general formula I are additionally preferred in which

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ and OCH₃ ;

R¹ is halogen, C₁ -C₄ -alkyl, C₁ -C₂ -haloalkyl, C₁ -C₂ -alkoxy, C₁ -C₂-haloalkoxy, C₁ -C₂ -alkylthio or phenyl;

n is 0 or 1;

X is O or S;

R² is unsubstituted or substituted C₁ -C₄ -alkyl or unsubstituted orsubstituted C₃ -C₆ -cycloalkyl.

In addition, compounds of the general formula I are preferred in whichR² --Y-- is one of the following five-membered ring heteroaromaticsystems ##STR6##

In addition, compounds of the general formula I are preferred in which

n is 0 or 1;

X is O or S;

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ and OCH₃ ;

R¹ is halogen, C₁ -C₄ -alkyl, C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₂-haloalkoxy, C₁ -C₂ -alkylthio or phenyl;

R² is an unsubstituted or substituted, mono- or binuclear aromatic ringsystem which, in addition to carbon atoms, can contain one to fournitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atomor an oxygen or sulfur atom as ring members.

Additionally, compounds of the general formula I are preferred in which

n is 0;

X is O;

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ and OCH₃ ;

R² is an unsubstituted or substituted, mono- or binuclear aromatic ringsystem which, in addition to carbon atoms, can contain one to fournitrogen atoms or one or two nitrogen atoms and an oxygen or sulfur atomor an oxygen or sulfur atom as ring members.

In addition, compounds of the general formula I are preferred in which

n is 0 or 1;

X is O or S;

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ and OCH₃ ;

R¹ is halogen, C₁ -C₄ -alkyl, C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₂-haloalkoxy, C₁ -C₂ -alkylthio or phenyl;

R² is unsubstituted or substituted phenyl.

In addition, compounds of the general formula I are preferred in which

n is 0;

X is O;

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ and OCH₃ ;

R² is unsubstituted or substituted phenyl.

Compounds of the general formula I are further preferred in which

n is 0 or 1;

X is O or S;

Y is a five-membered ring heteroaromatic system which, in addition toR², can also carry one or two radicals from the group consisting of Cl,CH₃, CF₃ or OCH₃ ;

R¹ is halogen, C₁ -C₄ -alkyl, C₁ -C₂ -haloalkyl, C₁ -C₄ -alkoxy, C₁ -C₂-haloalkoxy, C₁ -C₂ -alkylthio or phenyl;

R² is unsubstituted or substituted five-membered ring heteroaromatics.

Compounds of the general formula I are additionally preferred in which

n is 0 or 1;

X is O or S;

Y is a six-membered ring heteroaromatic system which, in addition to R²,can also carry one or two radicals from the group consisting of Cl, CH₃,CF₃ and OCH₃ ;

R² is unsubstituted or substituted six-membered ring heteroaromatics.

Particularly preferred compounds of the formula I.1, I.2, I.3, I.4, I.5,I.6, I.7, I.8, I.9, I.10, I.11 and I.12 are summarized in the TablesA.1, A.2, A.3, A.4, A.5, A.6, A.7, A.8, A.9, A.10, A.11 and A.12 below.

TABLES

                  TABLE A.1                                                       ______________________________________                                                                       I.1                                                                             #STR7##                                         -                                                                          No.        R.sup.1.sub.n                                                                            R.sup.2                                                 ______________________________________                                        1.001      H          C.sub.6 H.sub.5                                           1.002         3-Cl      C.sub.6 H.sub.5                                       1.003         4-Cl      C.sub.6 H.sub.5                                       1.004         6-Cl      C.sub.6 H.sub.5                                       1.005         4-F       C.sub.6 H.sub.5                                       1.006         4-OCH.sub.3    C.sub.6 H.sub.5                                  1.007         3-CH.sub.3     C.sub.6 H.sub.5                                  1.008         6-CH.sub.3     C.sub.6 H.sub.5                                  1.009         H         2-F--C.sub.6 H.sub.4                                  1.010         H         3-F--C.sub.6 H.sub.4                                  1.011         H         4-F--C.sub.6 H.sub.4                                  1.012         H          2,3-F.sub.2 --C.sub.6 H.sub.3                        1.013         H          2,4-F.sub.2 --C.sub.6 H.sub.3                        1.014          H         2,5-F.sub.2 --C.sub.6 H.sub.3                        1.015          H         2,6-F.sub.2 --C.sub.6 H.sub.3                        1.016          H         3,4-F.sub.2 --C.sub.6 H.sub.3                        1.017          H         3,5-F.sub.2 --C.sub.6 H.sub.3                        1.018          H         2-Cl--C.sub.6 H.sub.4                                1.019          H         3-Cl--C.sub.6 H.sub.4                                1.020          H         4-Cl--C.sub.6 H.sub.4                                1.021          3-Cl      4-Cl--C.sub.6 H.sub.4                                1.022          4-Cl      4-Cl--C.sub.6 H.sub.4                                1.023          6-Cl      4-Cl--C.sub.6 H.sub.4                                1.024          4-F       4-Cl--C.sub.6 H.sub.4                                1.025       4-OCH.sub.3   4-Cl--C.sub.6 H.sub.4                               1.026       3-CH.sub.3     4-Cl--C.sub.6 H.sub.4                              1.027       6-CH.sub.3     4-Cl--C.sub.6 H.sub.4                              1.028         H         2,3-Cl.sub.2 --C.sub.6 H.sub.3                        1.029         H          2,4-Cl.sub.2 --C.sub.6 H.sub.3                       1.030         H          2,5-Cl.sub.2 --C.sub.6 H.sub.3                       1.031         H          2,6-Cl.sub.2 --C.sub.6 H.sub.3                       1.032         H          3,4-Cl.sub.2 --C.sub.6 H.sub.3                       1.033       H           3,5-Cl.sub.2 --C.sub.6 H.sub.3                        1.034       H           2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                      1.035       H           2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                      1.036       H           2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                      1.037       H           2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      1.038       H           2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                      1.039       H           3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      1.040       H           2-Br--C.sub.6 H.sub.4                                 1.041       H           3-Br--C.sub.6 H.sub.4                                 1.042      H           4-Br--C.sub.6 H.sub.4                                  1.043      H           2,4-Br.sub.2 --C.sub.6 H.sub.3                         1.044      H           2-Br, 4-F--C.sub.6 H.sub.3                             1.045       H          2-Br, 4-Cl--C.sub.6 H.sub.3                            1.046       H          2-F,  4-Cl--C.sub.6 H.sub.3                            1.047       H           3-F, 4-Cl--C.sub.6 H.sub.3                            1.048       H           3-Cl, 5-F--C.sub.6 H.sub.3                            1.049       H           2-Cl, 4-F--C.sub.6 H.sub.3                            1.050       H           2-CN--C.sub.6 H.sub.4                                 1.051       H           3-CN--C.sub.6 H.sub.4                                 1.052       H           4-CN--C.sub.6 H.sub.4                                 1.053       H           3-CN, 4-Cl--C.sub.6 H.sub.3                           1.054       H          4-NO.sub.2 --C.sub.6 H.sub.4                           1.055      H           4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                1.056     H           2-CH.sub.3 --C.sub.6 H.sub.4                            1.057     H           3-CH.sub.3 --C.sub.6 H.sub.4                            1.058     H           4-CH.sub.3 --C.sub.6 H.sub.4                            1.059     H           2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.060       H         2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.061      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.062      H          2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.063      H          3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.064      H          3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  1.065       H         2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                1.066      H          3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                1.067      H          2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                       1.068      H          2-Cl,  4-CH.sub.3 --C.sub.6 H.sub.3                     1.069      H          3-CH.sub.3,  4-Cl--C.sub.6 H.sub.3                      1.070      H          3-Cl,  5-CH.sub.3 --C.sub.6 H.sub.3                     1.071      H          2-CN,  4-CH.sub.3 --C.sub.6 H.sub.3                     1.072     H          2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                        1.073      H         4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                     1.074      H         4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                  1.075       H        3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                     1.076      H         4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                     1.077      H         2-CF.sub.3 --C.sub.6 H.sub.4                             1.078       H          3-CF.sub.3 --C.sub.6 H.sub.4                           1.079       H          4-CF.sub.3 --C.sub.6 H.sub.4                           1.080       H          3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                 1.081       H          2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                     1.082       H          2-OCH.sub.3 --C.sub.6 H.sub.4                          1.083       H          3-OCH.sub.3 --C.sub.6 H.sub.4                          1.084     H            4-OCH.sub.3 --C.sub.6 H.sub.4                          1.085       H          2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                1.086       H          3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                1.087       H          2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                1.088       H          3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                1.089       H          3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                                   1.090       H          2-CH.sub.3,  4-OCH.sub.3                              --C.sub.6 H.sub.3                                         1.091       H          2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                    1.092       H          4-OCF.sub.3 --C.sub.6 H.sub.4                          1.093       H          2-OCHF.sub.2 --C.sub.6 H.sub.4                         1.094       H          3-OCHF.sub.2 --C.sub.6 H.sub.4                         1.095       H          4-OCHF.sub.2 --C.sub.6 H.sub.4                         1.096       H          4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                                    1.097       H          2-F, 4-OCHF.sub.2 --C.sub.6                           H.sub.3                                                   1.098       H          4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                1.099       H          4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                                    1.100       H          3-(CO.sub.2 CH.sub.3)--C.sub                          .6 H.sub.4                                                1.101       H          4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                 1.102       H          4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4       1.103       H          2,3-[O--CH.sub.2 --O)--C.sub.6 H.sub.3                 1.104       H          3,4-[O--CH.sub.2 --O)--C.sub.6 H.sub.3                 1.105       H          3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                             1.106       H          3,4-[O--CH.sub.2 CH.sub.2                             --O]--C.sub.6 H.sub.3                                     1.107       H          2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                                    1.108       H          3,4-[(CH.sub.2).sub.4                                 ]--C.sub.6 H.sub.3                                        1.109       H          2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6                                 H.sub.3                                                   1.110       H          3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                                 1.111       H          CH.sub.3                          1.112       H          CH.sub.2 CH.sub.3                                      1.113       H          CH.sub.2 CH.sub.2 CH.sub.3                             1.114       H          C(CH.sub.3).sub.2                                      1.115       H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                    1.116       H          CHCH(CH.sub.3).sub.2                                   1.117       H          CH(CH.sub.3)CH.sub.2 CH.sub.3                          1.118       H          C(CH.sub.3).sub.3                                      1.119       H          cyclopropyl                                            1.120       H          cyclohexyl                                             1.121       H          2-tetrahydrofuranyl                                    1.122       H          3-tetrahydrofuranyl                                    1.123      H        3-tetrahydrothienyl                                       1.124      H        2-1,3-dioxolenyl [sic]                                    1.125      H        2-1,3-dioxanyl                                            1.126      H        4-tetrahydropyranyl                                     ______________________________________                                    

                  TABLE A.2                                                       ______________________________________                                                                       I.2                                                                             #STR8##                                         -                                                                          No.        R.sup.1.sub.n                                                                            R.sup.2                                                 ______________________________________                                          2.001         H          C.sub.6 H.sub.5                                      2.002         3-Cl       C.sub.6 H.sub.5                                      2.003         4-Cl       C.sub.6 H.sub.5                                      2.004         6-Cl       C.sub.6 H.sub.5                                      2.005         4-F        C.sub.6 H.sub.5                                      2.006         4-OCH.sub.3     C.sub.6 H.sub.5                                 2.007         3-CH.sub.3      C.sub.6 H.sub.5                                 2.008         6-CH.sub.3      C.sub.6 H.sub.5                                 2.009         H          2-F--C.sub.6 H.sub.4                                 2.010         H          3-F--C.sub.6 H.sub.4                                 2.011         H          4-F--C.sub.6 H.sub.4                                 2.012         H          2,3-F.sub.2 --C.sub.6 H.sub.3                        2.013         H          2,4-F.sub.2 --C.sub.6 H.sub.3                        2.014         H          2,5-F.sub.2 --C.sub.6 H.sub.3                        2.015         H          2,6-F.sub.2 --C.sub.6 H.sub.3                        2.016         H          3,4-F.sub.2 --C.sub.6 H.sub.3                        2.017         H          3,5-F.sub.2 --C.sub.6 H.sub.3                        2.018         H          2-Cl--C.sub.6 H.sub.4                                2.019         H          3-Cl--C.sub.6 H.sub.4                                2.020         H          4-Cl--C.sub.6 H.sub.4                                2.021         3-Cl       4-Cl--C.sub.6 H.sub.4                                2.022         4-Cl       4-Cl--C.sub.6 H.sub.4                                2.023         6-Cl       4-Cl--C.sub.6 H.sub.4                                2.024         4-F        4-Cl--C.sub.6 H.sub.4                                2.025      4-OCH.sub.3    4-Cl--C.sub.6 H.sub.4                               2.026      3-CH.sub.3     4-Cl--C.sub.6 H.sub.4                               2.027      6-CH.sub.3     4-Cl--C.sub.6 H.sub.4                               2.028     H          2,3-Cl.sub.2 --C.sub.6 H.sub.3                           2.029     H          2,4-Cl.sub.2 --C.sub.6 H.sub.3                           2.030     H          2,5-Cl.sub.2 --C.sub.6 H.sub.3                           2.031     H          2,6-Cl.sub.2 --C.sub.6 H.sub.3                           2.032     H          3,4-Cl.sub.2 --C.sub.6 H.sub.3                           2.033     H          3,5-Cl.sub.2 --C.sub.6 H.sub.3                           2.034     H          2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                         2.035     H          2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                         2.036     H          2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                         2.037     H          2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                         2.038     H          2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                         2.039     H          3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                         2.040     H          2-Br--C.sub.6 H.sub.4                                    2.041     H          3-Br--C.sub.6 H.sub.4                                    2.042     H          4-Br--C.sub.6 H.sub.4                                    2.043      H         2,4-Br.sub.2 --C.sub.6 H.sub.3                           2.044      H          2-Br,  4-F--C.sub.6 H.sub.3                             2.045      H          2-Br,  4-Cl--C.sub.6 H.sub.3                            2.046      H          2-F, 4-Cl--C.sub.6 H.sub.3                              2.047      H          3-F, 4-Cl--C.sub.6 H.sub.3                              2.048      H          3-Cl,  5-F--C.sub.6 H.sub.3                             2.049      H          2-Cl,  4-F--C.sub.6 H.sub.3                             2.050      H          2-CN--C.sub.6 H.sub.4                                   2.051      H          3-CN--C.sub.6 H.sub.4                                   2.052      H          4-CN--C.sub.6 H.sub.4                                   2.053      H          3-CN, 4-Cl--C.sub.6 H.sub.3                             2.054      H          4-NO.sub.2 --C.sub.6 H.sub.4                            2.055      H          4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                 2.056      H          2-CH.sub.3 --C.sub.6 H.sub.4                            2.057      H          3-CH.sub.3 --C.sub.6 H.sub.4                            2.058      H          4-CH.sub.3 --C.sub.6 H.sub.4                            2.059      H          2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.060      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.061      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.062      H          2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.063      H          3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.064      H          3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  2.065      H          2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                2.066      H          3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                2.067      H          2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                       2.068      H          2-Cl,  4-CH.sub.3 --C.sub.6 H.sub.3                     2.069      H          3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                       2.070      H          3-Cl,  5-CH.sub.3 --C.sub.6 H.sub.3                     2.071      H          2-CN,  4-CH.sub.3 --C.sub.6 H.sub.3                     2.072      H          2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                       2.073       H          4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                   2.074       H          4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                2.075       H          3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                   2.076       H          4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                   2.077       H          2-CF.sub.3 --C.sub.6 H.sub.4                           2.078       H          3-CF.sub.3 --C.sub.6 H.sub.4                           2.079       H          4-CF.sub.3 --C.sub.6 H.sub.4                           2.080       H          3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                 2.081       H          2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                     2.082       H          2-OCH.sub.3 --C.sub.6 H.sub.4                          2.083       H          3-OCH.sub.3 --C.sub.6 H.sub.4                          2.084       H          4-OCH.sub.3 --C.sub.6 H.sub.4                          2.085       H          2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                2.086       H          3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                2.087       H          2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                2.088       H          3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                2.089       H          3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                                   2.090       H          2-CH.sub.3, 4-OCH.sub.3                               --C.sub.6 H.sub.3                                         2.091       H          2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                    2.092       H          4-OCF.sub.3 --C.sub.6 H.sub.4                          2.093       H          2-OCHF.sub.2 --C.sub.6 H.sub.4                         2.094       H          3-OCHF.sub.2 --C.sub.6 H.sub.4                         2.095       H          4-OCHF.sub.2 --C.sub.6 H.sub.4                         2.096       H          4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                                    2.097       H          2-F, 4-OCHF.sub.2 --C.sub.6                           H.sub.3                                                   2.098       H          4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                2.099       H          4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                                    2.100       H          3-(CO.sub.2 CH.sub.3)--C.sub                          .6 H.sub.4                                                2.101       H          4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                 2.102       H          4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4       2.103       H          2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                 2.104       H          3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                 2.105       H          3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                             2.106       H          3,4-[O--CH.sub.2 CH.sub.2                             --O]--C.sub.6 H.sub.3                                     2.107       H          2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                                    2.108       H          3,4-[(CH.sub.2).sub.4                                 ]--C.sub.6 H.sub.3                                        2.109       H          2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6                                 H.sub.3                                                   2.110       H          3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                                 2.111       H          CH.sub.3                          2.112       H          CH.sub.2 CH.sub.3                                      2.113       H          CH.sub.2 CH.sub.2 CH.sub.3                             2.114       H          C(CH.sub.3).sub.2                                      2.115       H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                    2.116       H          CHCH(CH.sub.3).sub.2                                   2.117       H          CH(CH.sub.3)CH.sub.2 CH.sub.3                          2.118     H         C(CH.sub.3).sub.3                                         2.119     H         cyclopropyl                                               2.120     H         cyclohexyl                                                2.121     H         2-tetrahydrofuranyl                                       2.122     H         3-tetrahydrofuranyl                                       2.123     H         3-tetrahydrothienyl                                       2.124     H         2-1,3-dioxolanyl                                          2.125     H         2-1,3-dioxanyl                                            2.126     H         4-tetrahydropyranyl                                     ______________________________________                                    

                  TABLE A.3                                                       ______________________________________                                                                       I.3                                                                             #STR9##                                         -                                                                          No.        R.sup.1.sub.n                                                                            R.sup.2                                                 ______________________________________                                        3.001      H          C.sub.6 H.sub.5                                           3.002       3-Cl       C.sub.6 H.sub.5                                        3.003       4-Cl       C.sub.6 H.sub.5                                        3.004       6-Cl       C.sub.6 H.sub.5                                        3.005       4-F        C.sub.6 H.sub.5                                        3.006       4-OCH.sub.3     C.sub.6 H.sub.5                                   3.007       3-CH.sub.3      C.sub.6 H.sub.5                                   3.008       6-CH.sub.3      C.sub.6 H.sub.5                                   3.009       H          2-F--C.sub.6 H.sub.4                                   3.010       H          3-F--C.sub.6 H.sub.4                                   3.011       H          4-F--C.sub.6 H.sub.4                                   3.012       H          2,3-F.sub.2 --C.sub.6 H.sub.3                          3.013       H          2,4-F.sub.2 --C.sub.6 H.sub.3                          3.014       H          2,5-F.sub.2 --C.sub.6 H.sub.3                          3.015       H          2,6-F.sub.2 --C.sub.6 H.sub.3                          3.016       H          3,4-F.sub.2 --C.sub.6 H.sub.3                          3.017       H          3,5-F.sub.2 --C.sub.6 H.sub.3                          3.018       H          2-Cl--C.sub.6 H.sub.4                                  3.019       H          3-Cl--C.sub.6 H.sub.4                                  3.020       H          4-Cl--C.sub.6 H.sub.4                                  3.021       3-Cl       4-Cl--C.sub.6 H.sub.4                                  3.022      4-Cl       4-Cl--C.sub.6 H.sub.4                                   3.023       6-Cl        4-Cl--C.sub.6 H.sub.4                                 3.024       4-F         4-Cl--C.sub.6 H.sub.4                                 3.025       4-OCH.sub.3      4-Cl--C.sub.6 H.sub.4                            3.026       3-CH.sub.3       4-Cl--C.sub.6 H.sub.4                            3.027       6-CH.sub.3       4-Cl--C.sub.6 H.sub.4                            3.028       H           2,3-Cl.sub.2 --C.sub.6 H.sub.3                        3.029       H           2,4-Cl.sub.2 --C.sub.6 H.sub.3                        3.030       H           2,5-Cl.sub.2 --C.sub.6 H.sub.3                        3.031      H           2,6-Cl.sub.2 --C.sub.6 H.sub.3                         3.032      H           3,4-Cl.sub.2 --C.sub.6 H.sub.3                         3.033      H           3,5-Cl.sub.2 --C.sub.6 H.sub.3                         3.034      H            2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                      3.035       H           2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                      3.036       H           2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                      3.037       H           2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      3.038       H           2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                      3.039       H           3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      3.040       H           2-Br--C.sub.6 H.sub.4                                 3.041       H           3-Br--C.sub.6 H.sub.4                                 3.042       H           4-Br--C.sub.6 H.sub.4                                 3.043       H           2,4-Br.sub.2 --C.sub.6 H.sub.3                        3.044       H          2-Br, 4-F--C.sub.6 H.sub.3                             3.045      H           2-Br, 4-Cl--C.sub.6 H.sub.3                            3.046      H           2-F, 4-Cl--C.sub.6 H.sub.3                             3.047      H           3-F, 4-Cl--C.sub.6 H.sub.3                             3.048      H           3-Cl, 5-F--C.sub.6 H.sub.3                             3.049      H           2-Cl, 4-F--C.sub.6 H.sub.3                             3.050       H          2-CN--C.sub.6 H.sub.4                                  3.051       H          3-CN--C.sub.6 H.sub.4                                  3.052       H          4-CN--C.sub.6 H.sub.4                                  3.053       H          3-CN, 4-Cl--C.sub.6 H.sub.3                            3.054       H          4-NO.sub.2 --C.sub.6 H.sub.4                           3.055       H          4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                3.056       H          2-CH.sub.3 --C.sub.6 H.sub.4                           3.057       H          3-CH.sub.3 --C.sub.6 H.sub.4                           3.058       H          4-CH.sub.3 --C.sub.6 H.sub.4                           3.059      H          2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  3.060      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  3.061      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  3.062      H          2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  3.063      H          3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  3.064       H          3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                 3.065       H          2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                    3.066       H          3,4,5-(CH.sub.3).sub.3                                --C.sub.6 H.sub.2                                         3.067       H          2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                      3.068      H          2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                      3.069      H          3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                       3.070      H          3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                      3.071      H          2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                      3.072      H          2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                       3.073      H          4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                    3.074      H          4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                 3.075      H          3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                    3.076      H          4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                    3.077      H          2-CF.sub.3 --C.sub.6 H.sub.4                            3.078      H          3-CF.sub.3 --C.sub.6 H.sub.4                            3.079      H          4-CF.sub.3 --C.sub.6 H.sub.4                            3.080      H          3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                  3.081      H          2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                      3.082      H          2-OCH.sub.3 --C.sub.6 H.sub.4                           3.083      H          3-OCH.sub.3 --C.sub.6 H.sub.4                           3.084      H          4-OCH.sub.3 --C.sub.6 H.sub.4                           3.085      H          2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                 3.086      H          3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                 3.087      H          2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                 3.088      H          3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                 3.089      H          3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                                    3.090      H          2-CH.sub.3, 4-OCH.sub.3                                --C.sub.6 H.sub.3                                         3.091      H          2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                     3.092      H          4-OCF.sub.3 --C.sub.6 H.sub.4                           3.093      H          2-OCHF.sub.2 --C.sub.6 H.sub.4                          3.094      H          3-OCHF.sub.2 --C.sub.6 H.sub.4                          3.095      H          4-OCHF.sub.2 --C.sub.6 H.sub.4                          3.096      H          4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                3.097      H          2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                     3.098      H          4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                 3.099      H          4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                3.100      H          3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                  3.101      H          4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                  3.102      H          4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                             3.103      H          2,3-[O--CH.sub.2 --O]--C.sub.                          6 H.sub.3                                                 3.104      H          3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                  3.105      H          3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                              3.106      H          3,4-[O--CH.sub.2 CH.sub.2                              --O]--C.sub.6 H.sub.3                                     3.107      H          2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                3.108      H          3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                3.109      H          2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6                                  H.sub.3                                                   3.110      H          3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                                  3.111      H          CH.sub.3                           3.112      H          CH.sub.2 CH.sub.3                                       3.113       H         CH.sub.2 CH.sub.2 CH.sub.3                              3.114       H         C(CH.sub.3).sub.2                                       3.115       H         CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                     3.116       H         CHCH(CH.sub.3).sub.2                                    3.117       H         CH(CH.sub.3)CH.sub.2 CH.sub.3                           3.118       H         C(CH.sub.3).sub.3                                       3.119       H         cyclopropyl                                             3.120       H         cyclohexyl                                              3.121       H         2-tetrahydrofuranyl                                     3.122       H         3-tetrahydrofuranyl                                     3.123       H         3-tetrahydrothienyl                                     3.124       H         2-1,3-dioxolanyl                                        3.125       H         2-1,3-dioxanyl                                          3.126       H         4-tetrahydropyranyl                                   ______________________________________                                    

                  TABLE A.4                                                       ______________________________________                                                                       I.4                                                                             #STR10##                                        -                                                                          No.        R.sup.1.sub.n                                                                            R.sup.2                                                 ______________________________________                                        4.001      H          C.sub.6 H.sub.5                                           4.002      3-Cl        C.sub.6 H.sub.5                                        4.003      4-Cl        C.sub.6 H.sub.5                                        4.004      6-Cl        C.sub.6 H.sub.5                                        4.005      4-F         C.sub.6 H.sub.5                                        4.006      4-OCH.sub.3      C.sub.6 H.sub.5                                   4.007      3-CH.sub.3       C.sub.6 H.sub.5                                   4.008      6-CH.sub.3       C.sub.6 H.sub.5                                   4.009      H           2-F--C.sub.6 H.sub.4                                   4.010      H           3-F--C.sub.6 H.sub.4                                   4.011      H           4-F--C.sub.6 H.sub.4                                   4.012      H           2,3-F.sub.2 --C.sub.6 H.sub.3                          4.013      H           2,4-F.sub.2 --C.sub.6 H.sub.3                          4.014      H           2,5-F.sub.2 --C.sub.6 H.sub.3                          4.015      H           2,6-F.sub.2 --C.sub.6 H.sub.3                          4.016      H           3,4-F.sub.2 --C.sub.6 H.sub.3                          4.017      H           3,5-F.sub.2 --C.sub.6 H.sub.3                          4.018       H          2-Cl--C.sub.6 H.sub.4                                  4.019       H          3-Cl--C.sub.6 H.sub.4                                  4.020       H          4-Cl--C.sub.6 H.sub.4                                  4.021      3-Cl        4-Cl--C.sub.6 H.sub.4                                  4.022      4-Cl        4-Cl--C.sub.6 H.sub.4                                  4.023      6-Cl        4-Cl--C.sub.6 H.sub.4                                  4.024      4-F         4-Cl--C.sub.6 H.sub.4                                  4.025      4-OCH.sub.3      4-Cl--C.sub.6 H.sub.4                             4.026      3-CH.sub.3       4-Cl--C.sub.6 H.sub.4                             4.027      6-CH.sub.3       4-Cl--C.sub.6 H.sub.4                             4.028      H           2,3-Cl.sub.2 --C.sub.6 H.sub.3                         4.029      H           2,4-Cl.sub.2 --C.sub.6 H.sub.3                         4.030      H           2,5-Cl.sub.2 --C.sub.6 H.sub.3                         4.031      H           2,6-Cl.sub.2 --C.sub.6 H.sub.3                         4.032      H           3,4-Cl.sub.2 --C.sub.6 H.sub.3                         4.033      H           3,5-Cl.sub.2 --C.sub.6 H.sub.3                         4.034      H           2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                       4.035       H          2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                       4.036       H           2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                      4.037       H           2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      4.038       H           2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                      4.039       H           3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                      4.040       H           2-Br--C.sub.6 H.sub.4                                 4.041       H           3-Br--C.sub.6 H.sub.4                                 4.042       H           4-Br--C.sub.6 H.sub.4                                 4.043       H           2,4-Br.sub.2 --C.sub.6 H.sub.3                        4.044      H           2-Br, 4-F--C.sub.6 H.sub.3                             4.045      H           2-Br, 4-Cl--C.sub.6 H.sub.3                            4.046      H           2-F, 4-Cl--C.sub.6 H.sub.3                             4.047      H           3-F, 4-Cl--C.sub.6 H.sub.3                             4.048      H           3-Cl, 5-F--C.sub.6 H.sub.3                             4.049      H           2-Cl, 4-F--C.sub.6 H.sub.3                             4.050      H           2-CN--C.sub.6 H.sub.4                                  4.051      H           3-CN--C.sub.6 H.sub.4                                  4.052      H           4-CN--C.sub.6 H.sub.4                                  4.053       H          3-CN, 4-Cl--C.sub.6 H.sub.3                            4.054       H          4-NO.sub.2 --C.sub.6 H.sub.4                           4.055       H          4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                4.056       H          2-CH.sub.3 --C.sub.6 H.sub.4                           4.057       H          3-CH.sub.3 --C.sub.6 H.sub.4                           4.058       H          4-CH.sub.3 --C.sub.6 H.sub.4                           4.059       H          2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                 4.060      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  4.061      H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  4.062      H          2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  4.063        H        3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  4.064        H        3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                  4.065        H        2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                4.066        H        3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                4.067        H        2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                       4.068        H          2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                    4.069        H          3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                     4.070        H          3-Cl,  5-CH.sub.3 --C.sub.6 H.sub.3                   4.071      H          2-CN,  4-CH.sub.3 --C.sub.6 H.sub.3                     4.072       H          2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                      4.073       H          4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                   4.074       H          4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                4.075       H          3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                   4.076       H          4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                   4.077       H          2-CF.sub.3 --C.sub.6 H.sub.4                           4.078       H           3-CF.sub.3 --C.sub.6 H.sub.4                          4.079       H           4-CF.sub.3 --C.sub.6 H.sub.4                          4.080        H          3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                4.081        H          2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                    4.082        H          2-OCH.sub.3 --C.sub.6 H.sub.4                         4.083        H          3-OCH.sub.3 --C.sub.6 H.sub.4                         4.084       H           4-OCH.sub.3 --C.sub.6 H.sub.4                         4.085       H          2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                4.086        H          3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                                    4.087        H          2,5-(OCH.sub.3).sub.2                                --C.sub.6 H.sub.3                                         4.088       H          3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                4.089       H          3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                                   4.090       H          2-CH.sub.3, 4-OCH.sub.3                               --C.sub.6 H.sub.3                                         4.091       H          2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                    4.092       H          4-OCF.sub.3 --C.sub.6 H.sub.4                          4.093       H          2-OCHF.sub.2 --C.sub.6 H.sub.4                         4.094       H          3-OCHF.sub.2 --C.sub.6 H.sub.4                         4.095       H          4-OCHF.sub.2 --C.sub.6 H.sub.4                         4.096        H         4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                                    4.097        H         2-F, 4-OCHF.sub.2 --C.sub.6                           H.sub.3                                                   4.098        H         4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                4.099        H         4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                                    4.100       H         3-(CO.sub.2 CH.sub.3)--C.sub.                          6 H.sub.4                                                 4.101        H         4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                 4.102        H         4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4       4.103       H         2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                  4.104       H         3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                  4.105       H         3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                              4.106       H         3,4-[O--CH.sub.2 CH.sub.2                              --O]--C.sub.6 H.sub.3                                     4.107       H         2,3-[(CH.sub.2).sub.4)--C.sub.6 H.sub.3                 4.108        H          3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                                   4.109        H          2,3-(CH═CH.sub.2                                 --CH═CH)--C.sub.6 H.sub.3                             4.110        H          3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                                4.111        H          CH.sub.3                         4.112        H          CH.sub.2 CH.sub.3                                     4.113        H          CH.sub.2 CH.sub.2 CH.sub.3                            4.114        H          C(CH.sub.3).sub.2                                     4.115        H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                   4.116        H          CHCH(CH.sub.3).sub.2                                  4.117        H          CH(CH.sub.3)CH.sub.2 CH.sub.3                         4.118        H          C(CH.sub.3).sub.3                                     4.119        H          cyclopropyl                                           4.120        H          cyclohexyl                                            4.121        H          2-tetrahydrofuranyl                                   4.122        H          3-tetrahydrofuranyl                                   4.123        H          3-tetrahydrothienyl                                   4.124        H          2-1,3-doxolanyl [sic]                                 4.125        H          2-1,3-dioxanyl                                        4.126        H          4-tetrahydropyranyl                                 ______________________________________                                    

                  TABLE A.5                                                       ______________________________________                                                                       I.5                                                                             #STR11##                                        -                                                                          No.        R.sup.1.sub.n                                                                            R.sup.2                                                 ______________________________________                                        5.001      H          C.sub.6 H.sub.5                                           5.002       3-Cl       C.sub.6 H.sub.5                                        5.003       4-Cl       C.sub.6 H.sub.5                                        5.004       6-Cl       C.sub.6 H.sub.5                                        5.005       4-F        C.sub.6 H.sub.5                                        5.006       4-0CH.sub.3     C.sub.6 H.sub.5                                   5.007       3-CH.sub.3      C.sub.6 H.sub.5                                   5.008       6-CH.sub.3      C.sub.6 H.sub.5                                   5.009       H          2-F--C.sub.6 H.sub.4                                   5.010       H          3-F--C.sub.6 H.sub.4                                   5.011       H          4-F--C.sub.6 H.sub.4                                   5.012       H          2,3-F.sub.2 --C.sub.6 H.sub.3                          5.013        H           2,4-F.sub.2 --C.sub.6 H.sub.3                        5.014        H           2,5-F.sub.2 --C.sub.6 H.sub.3                        5.015        H           2,6-F.sub.2 --C.sub.6 H.sub.3                        5.016        H           3,4-F.sub.2 --C.sub.6 H.sub.3                        5.017        H           3,5-F.sub.2 --C.sub.6 H.sub.3                        5.018        H           2-Cl--C.sub.6 H.sub.4                                5.019        H           3-Cl--C.sub.6 H.sub.4                                5.020        H           4-Cl--C.sub.6 H.sub.4                                5.021      3-Cl        4-Cl--C.sub.6 H.sub.4                                  5.022      4-Cl        4-Cl--C.sub.6 H.sub.4                                  5.023      6-Cl        4-Cl--C.sub.6 H.sub.4                                  5.024      4-F         4-Cl--C.sub.6 H.sub.4                                  5.025      4-OCH.sub.3      4-Cl--C.sub.6 H.sub.4                             5.026      3-CH.sub.3       4-Cl--C.sub.6 H.sub.4                             5.027      6-CH.sub.3       4-Cl--C.sub.6 H.sub.4                             5.028        H           2,3-Cl.sub.2 --C.sub.6 H.sub.3                       5.029        H           2,4-Cl.sub.2 --C.sub.6 H.sub.3                       5.030        H           2,5-Cl.sub.2 --C.sub.6 H.sub.3                       5.031        H           2,6-Cl.sub.2 --C.sub.6 H.sub.3                       5.032        H           3,4-Cl.sub.2 --C.sub.6 H.sub.3                       5.033        H           3,5-Cl.sub.2 --C.sub.6 H.sub.3                       5.034        H           2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                     5.035        H           2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                     5.036        H           2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                     5.037        H           2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                     5.038        H           2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                     5.039        H           3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                     5.040        H           2-Br--C.sub.6 H.sub.4                                5.041        H           3-Br--C.sub.6 H.sub.4                                5.042        H           4-Br--C.sub.6 H.sub.4                                5.043         H         2,4-Br.sub.2 --C.sub.6 H.sub.3                        5.044         H          2-Br, 4-F--C.sub.6 H.sub.3                           5.045         H          2-Br, 4-Cl--C.sub.6 H.sub.3                          5.046         H          2-F, 4-Cl--C.sub.6 H.sub.3                           5.047         H          3-F, 4-Cl--C.sub.6 H.sub.3                           5.048         H          3-Cl, S-F--C.sub.6 H.sub.3                           5.049         H          2-Cl, 4-F--C.sub.6 H.sub.3                           5.050         H          2-CN--C.sub.6 H.sub.4                                5.051         H          3-CN--C.sub.6 H.sub.4                                5.052         H          4-CN--C.sub.6 H.sub.4                                5.053         H          3-CN, 4-Cl--C.sub.6 H.sub.3                          5.054         H          4-NO.sub.2 --C.sub.6 H.sub.4                         5.055         H          4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                                   5.056         H          2-CH.sub.3 --C.sub.6                                H.sub.4                                                   5.057         H          3-CH.sub.3 --C.sub.6 H.sub.4                         5.058        H          4-CH.sub.3 --C.sub.6 H.sub.4                          5.059        H          2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.060        H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.061        H          2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.062        H          2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.063        H          3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.064        H          3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                5.065        H          2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                                   5.066        H          3,4,5-(CH.sub.3).sub.3                               --C.sub.6 H.sub.2                                         5.067        H          2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                     5.068        H          2-Cl,  4-CH.sub.3 --C.sub.6 H.sub.3                   5.069        H          3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                     5.070        H          3-Cl,  5-CH.sub.3 --C.sub.6 H.sub.3                   5.071        H          2-CN,  4-CH.sub.3 --C.sub.6 H.sub.3                   5.072        H          2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                     5.073        H          4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                  5.074        H          4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                                    5.075        H          3-(C.sub.6 H.sub.5)--C.sub.                          6 H.sub.4                                                 5.076       H          4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                   5.077       H          2-CF.sub.3 --C.sub.6 H.sub.4                           5.078       H          3-CF.sub.3 --C.sub.6 H.sub.4                           5.079       H          4-CF.sub.3 --C.sub.6 H.sub.4                           5.080       H          3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                 5.081       H          2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                     5.082      H          2-OCH.sub.3 --C.sub.6 H.sub.4                           5.083       H          3-OCH.sub.3 --C.sub.6 H.sub.4                          5.084       H          4-OCH.sub.3 --C.sub.6 H.sub.4                          5.085       H          2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                5.086        H          3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                                    5.087        H          2,5-(OCH.sub.3).sub.2                                --C.sub.6 H.sub.3                                         5.088        H          3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                                    5.089        H          3,4,5-(OCH.sub.3).sub.3                              --C.sub.6 H.sub.2                                         5.090        H          2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                                  5.091        H          2-Cl, 4-OCH.sub.3 --C.sub.6                           H.sub.3                                                  5.092        H          4-OCF.sub.3 --C.sub.6 H.sub.4                         5.093        H          2-OCHF.sub.2 --C.sub.6 H.sub.4                        5.094        H          3-OCHF.sub.2 --C.sub.6 H.sub.4                        5.095       H          4-OCHF.sub.2 --C.sub.6 H.sub.4                         5.096        H          4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                                   5.097        H          2-F, 4-OCHF.sub.2 --C.sub.6                           H.sub.3                                                  5.098        H          4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                    5.099        H          4-[OC(CH.sub.3).sub.3                                ]--C.sub.6 H.sub.4                                        5.100       H          3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                 5.101        H          4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                5.102        H          4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6                                  H.sub.4                                                   5.103     H          2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                   5.104     H          3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                   5.105     H          3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                               5.106     H          3,4-[O--CH.sub.2 CH.sub.2                               --O]--C.sub.6 H.sub.3                                     5.107     H          2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                 5.108     H          3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                 5.109     H          2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3       5.110     H          3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                                   5.111     H          CH.sub.3                            5.112     H          CH.sub.2 CH.sub.3                                        5.113     H          CH.sub.2 CH.sub.2 CH.sub.3                               5.114     H          C(CH.sub.3).sub.2                                        5.115     H          CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                      5.116     H          CHCH(CH.sub.3).sub.2                                     5.117     H          CH(CH.sub.3)CH.sub.2 CH.sub.3                            5.118     H          C(CH.sub.3).sub.3                                        5.119     H          cyclopropyl                                              5.120     H          cyclohexyl                                               5.121     H          2-tetrahydrofuranyl                                      5.122     H          3-tetrahydrofuranyl                                      5.123     H          3-tetrahydrothienyl                                      5.124     H          2-1,3-dioxolanyl                                         5.125     H          2-1,3-dioxanyl                                           5.126     H          4-tetrahydropyranyl                                    ______________________________________                                    

                  TABLE A.6                                                       ______________________________________                                                                       I.6                                                                             #STR12##                                        -                                                                          No.      R.sup.1.sub.n                                                                            R.sup.2                                                   ______________________________________                                        6.001    H          C.sub.6 H.sub.5                                             6.002 3-Cl C.sub.6 H.sub.5                                                    6.003 4-Cl C.sub.6 H.sub.5                                                    6.004 6-Cl C.sub.6 H.sub.5                                                    6.005 4-F C.sub.6 H.sub.5                                                     6.006 4-OCH.sub.3 C.sub.6 H.sub.5                                             6.007 3-CH.sub.3 C.sub.6 H.sub.5                                              6.008 6-CH.sub.3 C.sub.6 H.sub.5                                              6.009 H 2-F--C.sub.6 H.sub.4                                                  6.010 H 3-F--C.sub.6 H.sub.4                                                  6.011 H 4-F--C.sub.6 H.sub.4                                                  6.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                         6.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                         6.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                         6.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                         6.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                         6.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                         6.018 H 2-Cl--C.sub.6 H.sub.4                                                 6.019 H 3-Cl--C.sub.6 H.sub.4                                                 6.020 H 4-Cl--C.sub.6 H.sub.4                                                 6.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                              6.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                              6.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                              6.024 4-F 4-Cl--C.sub.6 H.sub.4                                               6.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                       6.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        6.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        6.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                        6.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                        6.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                        6.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                        6.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                        6.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                        6.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                      6.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                      6.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                      6.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      6.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                      6.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      6.040 H 2-Br--C.sub.6 H.sub.4                                                 6.041 H 3-Br--C.sub.6 H.sub.4                                                 6.042 H 4-Br--C.sub.6 H.sub.4                                                 6.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                        6.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                            6.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                           6.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                            6.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                            6.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                            6.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                            6.050 H 2-CN--C.sub.6 H.sub.4                                                 6.051 H 3-CN--C.sub.6 H.sub.4                                                 6.052 H 4-CN--C.sub.6 H.sub.4                                                 6.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                           6.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                          6.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                               6.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                          6.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                          6.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                          6.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                6.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              6.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              6.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     6.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                    6.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     6.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                    6.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                    6.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                     6.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                  6.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                               6.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  6.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  6.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                          6.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                          6.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                          6.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                                6.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                    6.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                         6.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                         6.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                         6.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               6.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               6.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               6.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               6.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                             6.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                             6.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                   6.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                         6.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                        6.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                        6.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                        6.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                              6.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                   6.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               6.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              6.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                6.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                6.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                      6.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                6.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                6.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                       6.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                       6.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              6.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              6.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                    6.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                           6.111 H CH.sub.3                                                              6.112 H CH.sub.2 CH.sub.3                                                     6.113 H CH.sub.2 CH.sub.2 CH.sub.3                                            6.114 H C(CH.sub.3).sub.2                                                     6.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                   6.116 H CHCH(CH.sub.3).sub.2                                                  6.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                         6.118 H C(CH.sub.3).sub.3                                                     6.119 H cyclopropyl                                                           6.120 H cyclohexyl                                                            6.121 H 2-tetrahydrofuranyl                                                   6.122 H 3-tetrahydrofuranyl                                                   6.123 H 3-tetrahydrothienyl                                                   6.124 H 2-1,3-dioxolanyl                                                      6.125 H 2-1,3-dioxanyl                                                        6.126 H 4-tetrahydropyranyl                                                 ______________________________________                                    

                  TABLE A.7                                                       ______________________________________                                                                       I.7                                                                             #STR13##                                        -                                                                          No.      R.sup.1.sub.n                                                                            R.sup.2                                                   ______________________________________                                        7.001    H          C.sub.6 H.sub.5                                             7.002 3-Cl C.sub.6 H.sub.5                                                    7.003 4-Cl C.sub.6 H.sub.5                                                    7.004 6-Cl C.sub.6 H.sub.5                                                    7.005 4-F C.sub.6 H.sub.5                                                     7.006 4-OCH.sub.3 C.sub.6 H.sub.5                                             7.007 3-CH.sub.3 C.sub.6 H.sub.5                                              7.008 6-CH.sub.3 C.sub.6 H.sub.5                                              7.009 H 2-F--C.sub.6 H.sub.4                                                  7.010 H 3-F--C.sub.6 H.sub.4                                                  7.011 H 4-F--C.sub.6 H.sub.4                                                  7.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                         7.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                         7.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                         7.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                         7.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                         7.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                         7.018 H 2-Cl--C.sub.6 H.sub.4                                                 7.019 H 3-Cl--C.sub.6 H.sub.4                                                 7.020 H 4-Cl--C.sub.6 H.sub.4                                                 7.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                              7.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                              7.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                              7.024 4-F 4-Cl--C.sub.6 H.sub.4                                               7.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                       7.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        7.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        7.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                        7.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                        7.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                        7.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                        7.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                        7.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                        7.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                      7.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                      7.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                      7.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      7.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                      7.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      7.040 H 2-Br--C.sub.6 H.sub.4                                                 7.041 H 3-Br--C.sub.6 H.sub.4                                                 7.042 H 4-Br--C.sub.6 H.sub.4                                                 7.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                        7.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                            7.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                           7.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                            7.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                            7.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                            7.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                            7.050 H 2-CN--C.sub.6 H.sub.4                                                 7.051 H 3-CN--C.sub.6 H.sub.4                                                 7.052 H 4-CN--C.sub.6 H.sub.4                                                 7.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                           7.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                          7.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                               7.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                          7.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                          7.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                          7.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                7.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              7.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              7.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     7.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                    7.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     7.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                    7.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                    7.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                     7.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                  7.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                               7.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  7.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  7.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                          7.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                          7.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                          7.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                                7.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                    7.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                         7.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                         7.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                         7.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               7.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               7.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               7.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               7.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                             7.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                             7.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                   7.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                         7.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                        7.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                        7.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                        7.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                              7.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                   7.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               7.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              7.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                7.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                7.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                      7.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                7.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                7.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                       7.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                       7.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              7.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              7.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                    7.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                           7.111 H CH.sub.3                                                              7.112 H CH.sub.2 CH.sub.3                                                     7.113 H CH.sub.2 CH.sub.2 CH.sub.3                                            7.114 H C(CH.sub.3).sub.2                                                     7.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                   7.116 H CHCH(CH.sub.3).sub.2                                                  7.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                         7.118 H C(CH.sub.3).sub.3                                                     7.119 H cyclopropyl                                                           7.120 H cyclohexyl                                                            7.121 H 2-tetrahydrofuranyl                                                   7.122 H 3-tetrahydrofuranyl                                                   7.123 H 3-tetrahydrothienyl                                                   7.124 H 2-1,3-dioxolanyl                                                      7.125 H 2-1,3-dioxanyl                                                        7.126 H 4-tetrahydropyranyl                                                 ______________________________________                                    

                  TABLE A.8                                                       ______________________________________                                                                       I.8                                                                             #STR14##                                        -                                                                          No.      R.sup.1.sub.n                                                                            R.sup.2                                                   ______________________________________                                        8.001    H          C.sub.6 H.sub.5                                             8.002 3-Cl C.sub.6 H.sub.5                                                    8.003 4-Cl C.sub.6 H.sub.5                                                    8.004 6-Cl C.sub.6 H.sub.5                                                    8.005 4-F C.sub.6 H.sub.5                                                     8.006 4-OCH.sub.3 C.sub.6 H.sub.5                                             8.007 3-CH.sub.3 C.sub.6 H.sub.5                                              8.008 6-CH.sub.3 C.sub.6 H.sub.5                                              8.009 H 2-F--C.sub.6 H.sub.4                                                  8.010 H 3-F--C.sub.6 H.sub.4                                                  8.011 H 4-F--C.sub.6 H.sub.4                                                  8.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                         8.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                         8.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                         8.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                         8.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                         8.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                         8.018 H 2-Cl--C.sub.6 H.sub.4                                                 8.019 H 3-Cl--C.sub.6 H.sub.4                                                 8.020 H 4-Cl--C.sub.6 H.sub.4                                                 8.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                              8.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                              8.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                              8.024 4-F 4-Cl--C.sub.6 H.sub.4                                               8.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                       8.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        8.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        8.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                        8.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                        8.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                        8.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                        8.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                        8.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                        8.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                      8.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                      8.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                      8.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      8.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                      8.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      8.040 H 2-Br--C.sub.6 H.sub.4                                                 8.041 H 3-Br--C.sub.6 H.sub.4                                                 8.042 H 4-Br--C.sub.6 H.sub.4                                                 8.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                        8.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                            8.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                           8.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                            8.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                            8.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                            8.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                            8.050 H 2-CN--C.sub.6 H.sub.4                                                 8.051 H 3-CN--C.sub.6 H.sub.4                                                 8.052 H 4-CN--C.sub.6 H.sub.4                                                 8.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                           8.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                          8.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                               8.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                          8.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                          8.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                          8.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                8.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              8.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              8.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     8.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                    8.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     8.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                    8.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                    8.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                     8.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                  8.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                               8.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  8.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  8.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                          8.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                          8.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                          8.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                                8.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                    8.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                         8.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                         8.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                         8.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               8.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               8.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               8.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               8.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                             8.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                             8.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                   8.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                         8.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                        8.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                        8.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                        8.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                              8.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                   8.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               8.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              8.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                8.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                8.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                      8.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                8.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                8.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                       8.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                       8.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              8.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              8.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                    8.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                           8.111 H CH.sub.3                                                              8.112 H CH.sub.2 CH.sub.3                                                     8.113 H CH.sub.2 CH.sub.2 CH.sub.3                                            8.114 H C(CH.sub.3).sub.2                                                     8.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                   8.116 H CHCH(CH.sub.3).sub.2                                                  8.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                         8.118 H C(CH.sub.3).sub.3                                                     8.119 H cyclopropyl                                                           8.120 H cyclohexyl                                                            8.121 H 2-tetrahydrofuranyl                                                   8.122 H 3-tetrahydrofuranyl                                                   8.123 H 3-tetrahydrothienyl                                                   8.124 H 2-1,3-dioxolanyl                                                      8.125 H 2-1,3-dioxanyl                                                        8.126 H 4-tetrahydropyranyl                                                 ______________________________________                                    

                  TABLE A.9                                                       ______________________________________                                                                       I.9                                                                             #STR15##                                        -                                                                          No.      R.sup.1.sub.n                                                                            R.sup.2                                                   ______________________________________                                        9.001    H          C.sub.6 H.sub.5                                             9.002 3-Cl C.sub.6 H.sub.5                                                    9.003 4-Cl C.sub.6 H.sub.5                                                    9.004 6-Cl C.sub.6 H.sub.5                                                    9.005 4-F C.sub.6 H.sub.5                                                     9.006 4-OCH.sub.3 C.sub.6 H.sub.5                                             9.007 3-CH.sub.3 C.sub.6 H.sub.5                                              9.008 6-CH.sub.3 C.sub.6 H.sub.5                                              9.009 H 2-F--C.sub.6 H.sub.4                                                  9.010 H 3-F--C.sub.6 H.sub.4                                                  9.011 H 4-F--C.sub.6 H.sub.4                                                  9.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                         9.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                         9.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                         9.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                         9.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                         9.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                         9.018 H 2-Cl--C.sub.6 H.sub.4                                                 9.019 H 3-Cl--C.sub.6 H.sub.4                                                 9.020 H 4-Cl--C.sub.6 H.sub.4                                                 9.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                              9.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                              9.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                              9.024 4-F 4-Cl--C.sub.6 H.sub.4                                               9.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                       9.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        9.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                        9.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                        9.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                        9.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                        9.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                        9.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                        9.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                        9.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                      9.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                      9.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                      9.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      9.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                      9.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                      9.040 H 2-Br--C.sub.6 H.sub.4                                                 9.041 H 3-Br--C.sub.6 H.sub.4                                                 9.042 H 4-Br--C.sub.6 H.sub.4                                                 9.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                        9.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                            9.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                           9.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                            9.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                            9.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                            9.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                            9.050 H 2-CN--C.sub.6 H.sub.4                                                 9.051 H 3-CN--C.sub.6 H.sub.4                                                 9.052 H 4-CN--C.sub.6 H.sub.4                                                 9.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                           9.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                          9.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                               9.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                          9.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                          9.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                          9.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                                9.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              9.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                              9.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     9.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                    9.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                     9.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                    9.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                    9.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                     9.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                  9.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                               9.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  9.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                  9.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                          9.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                          9.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                          9.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                                9.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                    9.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                         9.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                         9.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                         9.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               9.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               9.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               9.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                               9.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                             9.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                             9.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                   9.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                         9.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                        9.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                        9.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                        9.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                              9.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                   9.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               9.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              9.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                9.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                                9.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                      9.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                9.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                                9.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                       9.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                       9.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              9.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                              9.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                    9.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                           9.111 H CH.sub.3                                                              9.112 H CH.sub.2 CH.sub.3                                                     9.113 H CH.sub.2 CH.sub.2 CH.sub.3                                            9.114 H C(CH.sub.3).sub.2                                                     9.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                   9.116 H CHCH(CH.sub.3).sub.2                                                  9.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                         9.118 H C(CH.sub.3).sub.3                                                     9.119 H cyclopropyl                                                           9.120 H cyclohexyl                                                            9.121 H 2-tetrahydrofuranyl                                                   9.122 H 3-tetrahydrofuranyl                                                   9.123 H 3-tetrahydrothienyl                                                   9.124 H 2-1,3-dioxolanyl                                                      9.125 H 2-1,3-dioxanyl                                                        9.126 H 4-tetrahydropyranyl                                                 ______________________________________                                    

                  TABLE A.10                                                      ______________________________________                                                                      I.10                                                                            #STR16##                                         -                                                                          No.      R.sup.1.sub.n                                                                            R.sup.2                                                   ______________________________________                                        10.001   H          C.sub.6 H.sub.5                                             10.002 3-Cl C.sub.6 H.sub.5                                                   10.003 4-Cl C.sub.6 H.sub.5                                                   10.004 6-Cl C.sub.6 H.sub.5                                                   10.005 4-F C.sub.6 H.sub.5                                                    10.006 4-OCH.sub.3 C.sub.6 H.sub.5                                            10.007 3-CH.sub.3 C.sub.6 H.sub.5                                             10.008 6-CH.sub.3 C.sub.6 H.sub.5                                             10.009 H 2-F--C.sub.6 H.sub.4                                                 10.010 H 3-F--C.sub.6 H.sub.4                                                 10.011 H 4-F--C.sub.6 H.sub.4                                                 10.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                        10.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                        10.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                        10.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                        10.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                        10.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                        10.018 H 2-Cl--C.sub.6 H.sub.4                                                10.019 H 3-Cl--C.sub.6 H.sub.4                                                10.020 H 4-Cl--C.sub.6 H.sub.4                                                10.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                             10.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                             10.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                             10.024 4-F 4-Cl--C.sub.6 H.sub.4                                              10.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                      10.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                       10.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                       10.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                       10.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                       10.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                       10.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                       10.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                       10.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                       10.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                     10.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                     10.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                     10.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                     10.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                     10.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                     10.040 H 2-Br--C.sub.6 H.sub.4                                                10.041 H 3-Br--C.sub.6 H.sub.4                                                10.042 H 4-Br--C.sub.6 H.sub.4                                                10.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                       10.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                           10.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                          10.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                           10.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                           10.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                           10.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                           10.050 H 2-CN--C.sub.6 H.sub.4                                                10.051 H 3-CN--C.sub.6 H.sub.4                                                10.052 H 4-CN--C.sub.6 H.sub.4                                                10.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                          10.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                         10.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                              10.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                         10.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                         10.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                         10.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               10.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                             10.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                             10.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                    10.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                   10.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                    10.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                   10.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                   10.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                    10.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                 10.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              10.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                 10.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                 10.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                         10.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                         10.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                         10.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                               10.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                   10.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                        10.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                        10.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                        10.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              10.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              10.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              10.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              10.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                            10.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                            10.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                  10.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                        10.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                       10.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                       10.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                       10.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                             10.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                  10.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                              10.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                             10.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               10.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               10.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                     10.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                               10.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                               10.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                      10.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                      10.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                             10.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                             10.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                   10.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                          10.111 H CH.sub.3                                                             10.112 H CH.sub.2 CH.sub.3                                                    10.113 H CH.sub.2 CH.sub.2 CH.sub.3                                           10.114 H C(CH.sub.3).sub.2                                                    10.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                  10.116 H CHCH(CH.sub.3).sub.2                                                 10.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                        10.118 H C(CH.sub.3).sub.3                                                    10.119 H cyclopropyl                                                          10.120 H cyclohexyl                                                           10.121 H 2-tetrahydrofuranyl                                                  10.122 H 3-tetrahydrofuranyl                                                  10.123 H 3-tetrahydrothienyl                                                  10.124 H 2-1,3-dioxolanyl                                                     10.125 H 2-1,3-dioxanyl                                                       10.126 H 4-tetrahydropyranyl                                                ______________________________________                                    

                  TABLE A.11                                                      ______________________________________                                                                      I.11                                                                            #STR17##                                         -                                                                          No.       R.sub.n.sup.1                                                                           R.sup.2                                                   ______________________________________                                        11.001    H         C.sub.6 H.sub.5                                             11.002 3-Cl C.sub.6 H.sub.5                                                   11.003 4-Cl C.sub.6 H.sub.5                                                   11.004 6-Cl C.sub.6 H.sub.5                                                   11.005 4-F C.sub.6 H.sub.5                                                    11.006 4-OCH.sub.3 C.sub.6 H.sub.5                                            11.007 3-CH.sub.3 C.sub.6 H.sub.5                                             11.008 6-CH.sub.3 C.sub.6 H.sub.5                                             11.009 H 2-F--C.sub.6 H.sub.4                                                 11.010 H 3-F--C.sub.6 H.sub.4                                                 11.011 H 4-F--C.sub.6 H.sub.4                                                 11.012 H 2,3-F.sub.2 --C.sub.6 H.sub.3                                        11.013 H 2,4-F.sub.2 --C.sub.6 H.sub.3                                        11.014 H 2,5-F.sub.2 --C.sub.6 H.sub.3                                        11.015 H 2,6-F.sub.2 --C.sub.6 H.sub.3                                        11.016 H 3,4-F.sub.2 --C.sub.6 H.sub.3                                        11.017 H 3,5-F.sub.2 --C.sub.6 H.sub.3                                        11.018 H 2-Cl--C.sub.6 H.sub.4                                                11.019 H 3-Cl--C.sub.6 H.sub.4                                                11.020 H 4-Cl--C.sub.6 H.sub.4                                                11.021 3-Cl 4-Cl--C.sub.6 H.sub.4                                             11.022 4-Cl 4-Cl--C.sub.6 H.sub.4                                             11.023 6-Cl 4-Cl--C.sub.6 H.sub.4                                             11.024 4-F 4-Cl--C.sub.6 H.sub.4                                              11.025 4-OCH.sub.3 4-Cl--C.sub.6 H.sub.4                                      11.026 3-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                       11.027 6-CH.sub.3 4-Cl--C.sub.6 H.sub.4                                       11.028 H 2,3-Cl.sub.2 --C.sub.6 H.sub.3                                       11.029 H 2,4-Cl.sub.2 --C.sub.6 H.sub.3                                       11.030 H 2,5-Cl.sub.2 --C.sub.6 H.sub.3                                       11.031 H 2,6-Cl.sub.2 --C.sub.6 H.sub.3                                       11.032 H 3,4-Cl.sub.2 --C.sub.6 H.sub.3                                       11.033 H 3,5-Cl.sub.2 --C.sub.6 H.sub.3                                       11.034 H 2,3,4-Cl.sub.3 --C.sub.6 H.sub.2                                     11.035 H 2,3,5-Cl.sub.3 --C.sub.6 H.sub.2                                     11.036 H 2,3,6-Cl.sub.3 --C.sub.6 H.sub.2                                     11.037 H 2,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                     11.038 H 2,4,6-Cl.sub.3 --C.sub.6 H.sub.2                                     11.039 H 3,4,5-Cl.sub.3 --C.sub.6 H.sub.2                                     11.040 H 2-Br--C.sub.6 H.sub.4                                                11.041 H 3-Br--C.sub.6 H.sub.4                                                11.042 H 4-Br--C.sub.6 H.sub.4                                                11.043 H 2,4-Br.sub.2 --C.sub.6 H.sub.3                                       11.044 H 2-Br, 4-F--C.sub.6 H.sub.3                                           11.045 H 2-Br, 4-Cl--C.sub.6 H.sub.3                                          11.046 H 2-F, 4-Cl--C.sub.6 H.sub.3                                           11.047 H 3-F, 4-Cl--C.sub.6 H.sub.3                                           11.048 H 3-Cl, 5-F--C.sub.6 H.sub.3                                           11.049 H 2-Cl, 4-F--C.sub.6 H.sub.3                                           11.050 H 2-CN--C.sub.6 H.sub.4                                                11.051 H 3-CN--C.sub.6 H.sub.4                                                11.052 H 4-CN--C.sub.6 H.sub.4                                                11.053 H 3-CN, 4-Cl--C.sub.6 H.sub.3                                          11.054 H 4-NO.sub.2 --C.sub.6 H.sub.4                                         11.055 H 4-H.sub.2 N--C(═S)--C.sub.6 H.sub.4                              11.056 H 2-CH.sub.3 --C.sub.6 H.sub.4                                         11.057 H 3-CH.sub.3 --C.sub.6 H.sub.4                                         11.058 H 4-CH.sub.3 --C.sub.6 H.sub.4                                         11.059 H 2,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.060 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.061 H 2,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.062 H 2,6-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.063 H 3,4-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.064 H 3,5-(CH.sub.3).sub.2 --C.sub.6 H.sub.3                               11.065 H 2,4,6-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                             11.066 H 3,4,5-(CH.sub.3).sub.3 --C.sub.6 H.sub.2                             11.067 H 2-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                    11.068 H 2-Cl, 4-CH.sub.3 --C.sub.6 H.sub.3                                   11.069 H 3-CH.sub.3, 4-Cl--C.sub.6 H.sub.3                                    11.070 H 3-Cl, 5-CH.sub.3 --C.sub.6 H.sub.3                                   11.071 H 2-CN, 4-CH.sub.3 --C.sub.6 H.sub.3                                   11.072 H 2-CH.sub.3, 4-CN--C.sub.6 H.sub.3                                    11.073 H 4-(C.sub.2 H.sub.5)--C.sub.6 H.sub.4                                 11.074 H 4-[C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                              11.075 H 3-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                 11.076 H 4-(C.sub.6 H.sub.5)--C.sub.6 H.sub.4                                 11.077 H 2-CF.sub.3 --C.sub.6 H.sub.4                                         11.078 H 3-CF.sub.3 --C.sub.6 H.sub.4                                         11.079 H 4-CF.sub.3 --C.sub.6 H.sub.4                                         11.080 H 3,5-(CF.sub.3).sub.2 --C.sub.6 H.sub.3                               11.081 H 2-Cl, 4-CF.sub.3 --C.sub.6 H.sub.3                                   11.082 H 2-OCH.sub.3 --C.sub.6 H.sub.4                                        11.083 H 3-OCH.sub.3 --C.sub.6 H.sub.4                                        11.084 H 4-OCH.sub.3 --C.sub.6 H.sub.4                                        11.085 H 2,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              11.086 H 3,4-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              11.087 H 2,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              11.088 H 3,5-(OCH.sub.3).sub.2 --C.sub.6 H.sub.3                              11.089 H 3,4,5-(OCH.sub.3).sub.3 --C.sub.6 H.sub.2                            11.090 H 2-CH.sub.3, 4-OCH.sub.3 --C.sub.6 H.sub.3                            11.091 H 2-Cl, 4-OCH.sub.3 --C.sub.6 H.sub.3                                  11.092 H 4-OCF.sub.3 --C.sub.6 H.sub.4                                        11.093 H 2-OCHF.sub.2 --C.sub.6 H.sub.4                                       11.094 H 3-OCHF.sub.2 --C.sub.6 H.sub.4                                       11.095 H 4-OCHF.sub.2 --C.sub.6 H.sub.4                                       11.096 H 4-(OCF.sub.2 CHF.sub.2)--C.sub.6 H.sub.4                             11.097 H 2-F, 4-OCHF.sub.2 --C.sub.6 H.sub.3                                  11.098 H 4-(OCH.sub.2 CH.sub.3)--C.sub.6 H.sub.4                              11.099 H 4-[OC(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                             11.100 H 3-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               11.101 H 4-(CO.sub.2 CH.sub.3)--C.sub.6 H.sub.4                               11.102 H 4-[CO.sub.2 C(CH.sub.3).sub.3 ]--C.sub.6 H.sub.4                     11.103 H 2,3-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                               11.104 H 3,4-[O--CH.sub.2 --O]--C.sub.6 H.sub.3                               11.105 H 3,4-[O--C(CH.sub.3).sub.2 --O]--C.sub.6 H.sub.3                      11.106 H 3,4-[O--CH.sub.2 CH.sub.2 --O]--C.sub.6 H.sub.3                      11.107 H 2,3-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                             11.108 H 3,4-[(CH.sub.2).sub.4 ]--C.sub.6 H.sub.3                             11.109 H 2,3-(CH═CH.sub.2 --CH═CH)--C.sub.6 H.sub.3                   11.110 H 3,4-(CH═CH--CH═CH)--C.sub.6 H.sub.3                          11.111 H CH.sub.3                                                             11.112 H CH.sub.2 CH.sub.3                                                    11.113 H CH.sub.2 CH.sub.2 CH.sub.3                                           11.114 H C(CH.sub.3).sub.2                                                    11.115 H CH.sub.2 CH.sub.2 CH.sub.2 CH.sub.3                                  11.116 H CHCH(CH.sub.3).sub.2                                                 11.117 H CH(CH.sub.3)CH.sub.2 CH.sub.3                                        11.118 H C(CH.sub.3).sub.3                                                    11.119 H cyclopropyl                                                          11.120 H cyclohexyl                                                           11.121 H 2-tetrahydrofuranyl                                                  11.122 H 3-tetrahydrofuranyl                                                  11.123 H 3-tetrahydrothienyl                                                  11.124 H 2-1,3-dioxolanyl                                                     11.125 H 2-1,3-dioxanyl                                                       11.126 H 4-tetrahydropyranyl                                                ______________________________________                                    

                  TABLE A.12                                                      ______________________________________                                                                    I(X = O)                                                                        #STR18##                                           -                                                                          No.      R.sup.2 --Y                                                          ______________________________________                                        12.001   1-(2-pyridyl)pyrazol-4-yl                                              12.002 1-(3,5-di-trifluoromethyl-2-pyridyl)pyrazol-4-yl                       12.003 1-(5-chloro-3-trifluoromethyl-2-pyridyl)pyrazol-4-yl                   12.004 1-(6-trifluoromethyl-2-pyridyl)pyrazol-4-yl                            12.005 1-(4-trifluoromethyl-6-methyl-2-pyridyl)pyrazol-4-yl                   12.006 1-(1-ethyl-2-pyridyl)pyrazol-4-yl                                      12.007 1-(3-pyridyl)pyrazol-4-yl                                              12.008 1-(6-methyl-3-pyridyl)pyrazol-4-yl                                     12.009 1-(4-pyridyl)pyrazol-4-yl                                              12.010 1-(2,6-dimethyl-4-pyridyl)pyrazol-4-yl                                 12.011 1-(6-methyl-3-pyridazinyl)pyrazol-4-yl                                 12.012 1-(6-chloro-3-pyridazinyl)pyrazol-4-yl                                 12.013 1-(5-methoxycarbonyl-4-trifluoromethyl-2-pyrimidyl)-                    pyrazol-4-yl                                                                 12.014 1-(4-trifluoromethyl-2-pyrimidyl)pyrazol-4-yl                          12.015 1-(5-chloro-2-pyrimidyl)pyrazol-4-yl                                   12.016 1-(6-trifluoromethyl-4-pyrimidyl)pyrazol-4-yl                          12.017 1-(5-ethyl-2-pyrimidyl)pyrazol-4-yl                                    12.018 1-(2-methyl-5-pyrimidyl)pyrazol-4-yl                                   12.019 1-(5-methyl-2-pyrazinyl)pyrazol-4-yl                                   12.020 1-(5-chloro-2-pyrazinyl)pyrazol-4-yl                                   12.021 1-(4-methyl-2-thiazolyl)pyrazol-4-yl                                   12.022 1-(5-methyl-3-thiazolyl)pyrazol-4-yl                                   12.023 1-(5-cyclopropyl-3-isoxazolyl)pyrazol-4-yl                             12.024 1-(5-phenyl-3-isoxazolyl)pyrazol-4-yl                                  12.025 4-methylpyrazol-1-yl                                                   12.026 4-chloropyrazol-1-yl                                                   12.027 3,5-dimethylpyrazol-1-yl                                               12.028 4-phenylpyrazol-1-yl                                                   12.029 4-(3-methyl-5-isoxazolyl)pyrazol-1-yl                                  12.030 4-(3-tert-butyl-5-isoxazolyl)pyrazol-1-yl                              12.031 4-(3-phenyl-5-isoxazolyl)pyrazol-1-yl                                  12.032 4-(3-methyl-5-isoxazolyl)thiazol-2-yl                                  12.033 4-(3-isoxazolyl-5-isoxazolyl)thiazol-2-yl                              12.034 4-(2-methyl-4-thiazolyl)thiazol-2-yl                                   12.035 4-(2-hexyl-4-thiazolyl)thiazol-2-yl                                    12.036 2-(2-methyl-4-thiazolyl)-5-methylthiazol-4-yl                          12.037 4-(3-methyl-5-isoxazolyl)oxazol-2-yl                                   12.038 4-(3-methyl-4-thiazolyl)oxazol-2-yl                                    12.039 4-(2-cyclopropyl-4-thiazolyl)oxazol-2-yl                               12.040 4-(1-methoxyiminoethyl)thiazol-2-yl                                    12.041 4-(1-ethoxyiminoethyl)thiazol-2-yl                                     12.042 4-(1-prop-2-enyloxyiminoethyl)thiazol-2-yl                             12.043 4-(1-tert-butoxyiminoethyl)thiazol-2-yl                                12.044 4-(1-methoxyiminopropyl)thiazol-2-yl                                   12.045 4-(1-methoxyiminoethyl)-5-methylthiazol-2-yl                           12.046 4-(1-prop-2-enyloxyiminoethyl)-5-methylthiazol-2-yl                  ______________________________________                                    

The starting compounds IA can be prepared, for example, as describedbelow (Examples 1 to 3) from the easily accessible methylE-2-methoxyimino-2-[(2-methylphenoxymethyl)phenyl]acetate (cf. EP 493711) by aminolysis with methylamine and subsequent cleavage with borontrichloride or hydrogen bromide.

The procedures represented in the synthesis examples below were utilizedwith appropriate modification of the starting compounds for preparingfurther compounds I. The compounds thus obtained are listed in theTables below with physical data.

EXAMPLE 1

E-2-Methoxyimino-2-[(2-methylphenoxymethyl)phenyl]-N-methylacetamide

250 g of methylE-2-methoxyimino-2-[(2-methylphenoxymethyl)phenyl]acetate are suspendedin 1 l of 40% strength aqueous methylamine solution and heated to 40° C.for 4 h. After cooling to room temperature (20° C.), the solid isfiltered off with suction, washed several times with water and dried at50° C. 229.8 g of the title compound are obtained as colorless crystals.

M.p.: 109-112° C.

¹ H-NMR (CDCl₃, δ in ppm): 2.20 (s, 3H); 2.85 (d, 3H); 3.95 (s, 3H);4.90 (s, 2H); 6.7 (NH); 6.8-7.6 (m, 8H).

EXAMPLE 2 E-2-Methoxyimino-2-[(2-chloromethyl)phenyl]-N-methylacetamide

2 g ofE-2-methoxyimino-2-[(2-methylphenoxymethyl)phenyl]-N-methylacetamidefrom Example 1 are initially introduced into 30 ml of anhydrousdichloromethane at 10° C. 9.4 g of boron trichloride (as a 1-molarsolution in n-hexane) are added dropwise to this solution, it is heatedto reflux for 1.5 h and cooled to 10° C., a further 9.4 g of borontrichloride are added and the mixture is stirred overnight at roomtemperature (20° C.). After dropwise addition of 8.2 g of methanol, thebatch is concentrated in a rotary evaporator. The residue is taken up in100 ml of dichloromethane, and the solution is washed with 5% sodiumhydroxide solution and then with water. The organic phase is finallydried over sodium sulfate. After stripping off the solvent, 1.2 g of thetitle compound remain as an oil.

¹ H-NMR (CDCl₃, δ in ppm): 2.95 (d, 3H); 3.90 (s, 3H); 4.45 (s, 2H); 6.8(NH); 7.1-7.6 (m, 4H).

EXAMPLE 3 E-2-Methoxyimino-2-[(2-bromomethyl)phenyl]-N-methylacetamide

10 g ofE-2-methoxyimino-2-[(2-methylphenoxymethyl)phenyl]-N-methylacetamidefrom Example 1 are initially introduced into 50 ml of anhydrousdichloromethane. Hydrogen bromide is introduced into the solution up tothe saturation concentration (about 9 g of HBr). After stirring at roomtemperature for 68 h, the starting material is completely reacted. Afteraddition of a further 50 ml of dichloromethane, the mixture is worked upas in Example 2. 7.0 g of the title compound remain as an oil, whichcrystallizes completely on allowing to stand.

M.p.: 128-129° C.

¹ H-NMR (CDCl₃, δ in ppm): 2.95 (d, 3H); 3.95 (s, 3H); 4.35 (s, 2H);6.85 (NH); 7.1-7.5 (m, 4H).

EXAMPLE 4 MethylE-2-methoxyimino-2-[(2-[5-(4-chlorophenyl)isoxazol-3-yl]oxymethyl)phenyl]acetate

1.8 g of 3-hydroxy-5-(4-chlorophenyl)isoxazole are dissolved in 10 ml ofdimethylformamide. 1.6 g of finely powdered potassium carbonate and 2.8g of methyl E-2-methoxyimino-2-[(2-bromomethyl)phenyl]acetate are addedto this solution. The reaction mixture is stirred overnight at roomtemperature and then poured onto 50 ml of water for working up. Afterextracting three times with methyl tert-butyl ether, the combinedorganic phases are dried over sodium sulfate. After stripping off thesolvent, the residue is triturated with methyl tert-butyl ether. Afterfiltering off with suction, 1.8 g of the title compound remain.

M.p.: 155-157° C.

¹ H-NMR (CDCl₃, δ in ppm):

3.85 (s, 3H); 4.06 (s, 3H); 5.2 (s, 2H); 6.1 (s, 1H); 7.2-7.7 (m, 8H).

EXAMPLE 5E-2-Methoxyimino-2-[(2-[5-(4-chlorophenyl)isoxazol-3-yl]oxymethyl)phenyl]-N-methylacetamide

1.0 g of the methyl ester from Example 4 are dissolved in 15 ml oftetrahydrofuran and treated with 1 ml of 40% strength aqueousmethylamine solution. The mixture is stirred overnight at roomtemperature and concentrated, and the residue is taken up in 50 ml ofmethyl tert-butyl ether. The organic phase is extracted with water,dried over sodium sulfate and finally evaporated to dryness. 0.9 g ofthe title compound remains as a colorless solid.

M.p.: 195-198° C.

¹ H-NMR (CDCl₃, δ in ppm): 2.95 (d, 3H); 3.95 (s, 3H); 5.2 (s, 2H); 6.15(s, 1H); 6.85 (NH); 7.2-7.8 (m, 8H).

EXAMPLE 6E-2-Methoxyimino-2-[(2-[5-(4-trifluoromethylphenyl)-1,3,4-oxadiazol-2-yl]thiomethyl)phenyl]-N-methylacetamide

1.35 g of 5-(4-trifluoromethylphenyl)-2-mercapto-1,3,4-oxadiazole and1.43 g of the bromomethyl compound from Example 3 are dissolved in 30 mlof acetone. After addition of 0.8 g of finely powdered potassiumcarbonate, the batch is stirred overnight at RT. The solid is filteredoff with suction and the filtrate is evaporated to dryness. The residuewhich remains is triturated with n-pentane and filtered off withsuction. 2.2 g of the title compound remain as a colorless solid.

M.p.: 128-129° C.

¹ H-NMR (CDCl₃, δ in ppm): [lacuna]

EXAMPLE 7E-2-Methoxyimino-2-[(2-[1-(4-chloro-2-methylphenyl)pyrazol-4-yl]oxymethyl)phenyl]-N-methylacetamide

1.05 g of 1-(4-chloro-2-methylphenyl)-4-hydroxypyrazole are initiallyintroduced into 20 ml of dichloromethane. After addition of 50 mg oftetra-n-butylammonium iodide and a solution of 1.43 g of bromomethylcompound from Example 3 in 10 ml of dichloromethane, the reaction isstarted using 20 ml of 10% strength sodium hydroxide solution. Thetwo-phase system is vigorously stirred until conversion of thebromomethyl compound is complete. The organic phase is separated off andextracted a further two times with dichloromethane, and the combinedorganic phases are dried over sodium sulfate. The crude product whichremains after stripping off the solvent is taken up in 70 ml ofisopropyl ether/acetone (5:2, v/v). Insoluble constituents are decantedoff, the liquid is concentrated and the residue is chromatographed onsilica gel (eluent toluene/ethyl acetate, 9:1).

                                      TABLE 1                                     __________________________________________________________________________      #STR19##                                                                       -                                                                          No.                                                                              R.sub.n.sup.1                                                                    X R.sup.2 --Y         M.p. [° C.]/IR [cm.sup.-1 ]/.sup.1                                     H--NMR [ppm]                                      __________________________________________________________________________    1  H  O 5-Methylisoxazol-3-yl                                                                             112-115                                             2 H O 5-(4-chlorophenyl)isoxazol-3-yl 195-198                                 3 H O 3-Phenyl-1,2,4-thiadiazol-5-yl 3230,1652,1588,1462,1351                 5 H S 5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl 186-188                         6 H S 5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl 176-177                         7 H O 4-(4-Fluorophenyl)-1,3-thiazol-2-yl 118-120                             8 H O 4-(4-chlorophenyl)-1,3-thiazol-2-yl 121-123                             9 H O 4-(2,4-Dichlorophenyl)-1,3-thiazol-2-yl 120-121                         10 H O 1-Phenyl-1,2,4-triazol-3-yl 1667,1545,1329,1069,1038                   11 H O 1-Phenylpyrazol-4-yl 1667,1597,1580,1503,1400,                             1357,1035                                                                 12 H O 1-(4-Fluorophenyl)pyrazol-4-yl 1667,1514,1403,1358,1227,                                              1033                                           14 H O 1-(4-Trifluoromethylphenyl)pyrazol-4-yl 98-100                         15 H O 1-(4-Cyanophenyl)pyrazol-4-yl 130-135                                  16 H O 1-(4-Methylphenyl)pyrazol-4-yl 102-105                                 17 H O 1-(4-Chlorophenyl)pyrazol-4-yl 111-114                                 18 H O 1-(2,4-Dichlorophenyl)pyrazol-4-yl 104-106                             19 H O 5-Trifluoromethylisooxazol-3-yl [sic] 97-98                            20 H O 5-Phenylisoxazol-3-yl 121-123                                          21 H O 1-(6-Chloro-2-pyridyl)-1,2,4-triazol-3-yl 153-155                      22 H O 1-(2-Chloro-4-methylphenyl)pyrazol-4-yl                                23 H O 1-(2,4-Dichlorophenyl)pyrazol-3-yl 99-102                              24 H O 1-(4-Chlorophenyl)pyrazol-3-yl 110-122                                 25 H O 1-(3-Chlorophenyl)pyrazol-3-yl 1670,1596,1547,1475,1036                26 H O 1-(4-Fluorophenyl)pyrazol-3-yl 80-83                                   27 H d 1-(4-Methylphenyl)pyrazol-3-yl 3379,1662,1540,1353,1033                28 H S 1-Methylimidazol-2-yl 124-126                                          29 H S 4-Methyl-1,2,4-triazol-3-yl 131-135                                    30 H S 5-(4-Trifluoromethylphenyl)-1,3,4-oxadiazol- 128-129                      2-yl                                                                       31 H O 4-Acetylthiazol-2-yl 83-85                                             32 H O 4-Isopropylthiazol-2-yl 73-74                                          33 H O 4-Isobutylthiazol-2-yl 51-52                                           34 H O 4-Phenylthiazol-2-yl 128-130                                           35 H O 4-(2-Methylphenyl)thiazol-2-yl 88-89                                   36 H O 4-(3-Methylphenyl)thiazol-2-yl 91-92                                   37 H O 4-(4-Methylphenyl)thiazol-2-yl 118-119                                 38 H O 4-(2-Methoxyphenyl)thiazol-2-yl 1671,1533,1487,1462,1244,                                             1185,1036                                      39 H O 4-(3-Methoxyphenyl)thiazol-2-yl 113-114                                40 H O 4-(4-Methoxyphenyl)thiazol-2-yl 105-106                                41 H O 4-(3-Bromophenyl)thiazol-2-yl 110-112                                  42 H O 4-(4-Bromophenyl)thiazol-2-yl 122-124                                  43 H O 4-(3-Trifluoromethylphenyl)thiazol-2-yl 99-100                         44 H O 4-(4-Trifluoromethylphenyl)thiazol-2-y [sic] 115-117                   45 H O 2-(4-Fluorophenyl)-5-methylthiazol-4-yl 126                            46 H O 4-Phenyloxazol-2-yl 1670,1619,1602,1348,1036                           47 H O 5-Cyclopropylisoxazol-3-yl 3300,1671,1618,1509,1038                    48 H O 3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl 138-140                       49 H O 1-Phenylpyrazol-3-yl 80-83                                             50 H O 5-Methyl-1-phenylpyrazol-4-yl 3340,1668,1598,1503,1409,                    1036                                                                      51 H O 3-(4-Fluorophenyl)-1,2,4-thiadiazol-5-yl 105-110                       52 3-Cl O 1-(4-Chlorophenyl)pyrazol-3-yl 144-147                              53 3-Cl O 1-(4-Methylphenyl)pyrazol-3-yl 3350,1670,1543,1357,1039                                        54 3-Cl O 1-(4-chlorophenyl)pyrazol-4-yl                                     2.9(3H); 3.9(3H); 5.0(2H);                              6.8(NH); 7.1-7.6(9H)                                                      55 H O 4-(Methoxyiminoethyl)thiazol-2-yl 115-116                              56 H O 4-(Ethoxyiminoethyl)thiazol-2-yl 65-67                                 57 H O 5-(Methoxyiminoethyl)-4-methylthiazol-2-yl 104-106                     58 H O 5-(Ethoxyiminoethylyl)-4-methylthiazol-2-yl 3320,1617,1508,1378,1                                285,                                                    1048                                                                      59 H O 1-(n-Chlorophenyl)-1,2,4-triazol-3-yl 3310,1660,1551,1504,1333,                                       973                                            60 H O 1-(4-Chlorophenyl)-5-methyl-1,2,4-triazol-3-yl 3330,1670,1541,135                                0,1036                                              61 H O 1-Methyl-5-trifluoromethylpyrazol-3-yl 57-59                           62 H O 1-(2-Chlorophenyl)pyrazol-3-yl 80-82                                   63 H O 1-(2,4-Dimethylphenyl)pyrazol-3-yl 3240,1670,1541,1483,1360,                                          1036                                           64 H O 1-(4-Chlorophenyl)-3-methylpyrazol-4-yl 119-122                        65 H O 5-(5-Methyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 113-115                 66 H O 5-(5-Propyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 3325,2936,1659,152                                9,1346,                                                 1039                                                                      67 H O 5-(5-Hexyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 3295,2930,1660,1530                                ,1343,                                                  1040                                                                      68 3-Cl O 4-(4-Chlorophenyl)-1,3-thiazol-2-yl 68-71                           69 3-Cl O 4-(2,4-Dichlorophenyl)-1,3-thiazol-2-yl 128-130                     70 3-Cl O 1-(2,4-Dichlorophenyl)pyrazol-3-yl 128-129                          71 3-Cl O 1-(4-Chlorophenyl)-1,2,4-triazol-3-yl 171-173                       72 H O 1-(3,4-Dichlorophenyl)pyrazol-3-yl 3330,1670,1547,1474,1358,                                          1036                                           73 H O 1-(2,5-Dichlorophenyl)pyrazol-3-yl 3310,1670,1546,1490,1471,                                          1435,1035                                      74 H O 1-(3,5-Dichlorophenyl)pyrazol-3-yl 154-156                             75 H O 1-(4-Chloro-2-methylphenyl)pyrazol-3-yl 3320,1669,1543,1479,1350,          1034                                                                      76 H O 1-(4-Methoxyphenyl)pyrazol-3-yl 3330,1670,1542,1517,1360,                                             1034                                           77 H O 1-(3-Trifluoromethylphenyl)pyrazol-3-yl 114-116                        78 H O 1-(4-Chlorophenyl)-5-trifluoromethylpyrazol-3- 3330,1669,1567,150                                5,1139                                                 yl                                                                         79 H O 3-(4-Chlorophenyl)isoxazol-5-yl 142-145                                80 H O 5-Cyanoisoxazol-3-yl 2.9(3H); 4.0(3H); 5.15(2H);                           6.3(1H); 6.85(1H); 7.2-7.6                                                    (4H)                                                                      81 H O 5-Methyl-2-(pyrid-2-yl)-1,3-thiazol-4-yl 127-128                       82 H O 5-Methyl-2-(pyrid-3-yl)-1,3-thiazol-4-yl 148-149                       83 H O 5-Methyl-2-(pyrid-4-yl)-1,3-thiazol-4-yl 136-137                       84 H O 5-Methyl-2-(foran-2-yl)-1,3-thiazol-4-yl 100-102                       85 H O 5-Methyl-2-(thien-2-yl)-1,3-thiazol-4-yl 137-138                       86 H O 5-Methyl-2-(3-methylisoxazol-5-yl)-1,3- 120-122                           thiazol-4-yl                                                               87 H O 4-(3-Methylisoxazol-5-yl)-1,3-thiazol-2-yl 109-111                     88 H O 5-Methyl-2-(2-methyl-1,3-thiazol-4-yl)-1,3- 88-92                         thiazol-4-yl                                                               89 H O 4-(2,4-Dimethyl-1,3-thiazol-5-yl)-1,3- 129-130                            thiazol-4-yl                                                               90 H O 5-Methyl-2-(2-n-heptyl-1,3-thiazol-4-yl)- 72-74                           1,3-thiazol-4-yl                                                           91 H O 4-(2-n-Heptyl-1,3-thiazol-4-yl)-1,3-thiazol- 64-66                        2-yl [sic]                                                                 92 H O 1-(2-Methylphenyl)pyrazol-3-yl 3330,1672,1541,1360,1360,                                              1035                                           93 H O 1-(3-Methylphenyl)pyrazol-3-yl 3340,1671,1545,1358,1036                94 H O 5-Methyl-1-phenylpyrazol-3-yl 138-140                                __________________________________________________________________________

                                      TABLE 2                                     __________________________________________________________________________                                                II                                                                              #STR20##                           -                                                                          No.                                                                              R.sub.n.sup.1                                                                    X R.sup.2 --Y          M.p. [° C.]/IR [cm.sup.-1 ]/.sup.1                                     H--NMR [ppm]                                     __________________________________________________________________________    1  H  O 5-Methylisoxazol-3-yl                                                                              108-110                                            2 H O 5-(4-Chlorophenyl)isoxazol-3-yl 155-157                                 3 H O 3-Phenyl-1,2,4-thiadizol-5-yl [sic] 139-140                             4 H S 5-(4-Chlorophenyl)-1,3,4-oxadizaol-2-yl [sic] 103-105                   5 H S 5-(4-Methylphenyl)-1,3,4-oxadiazol-2-yl 135-136                         6 H O 4-(4-Fluorophenyl)-1,3-thiazol-2-yl 105-106                             7 H O 4-(4-Chlorophenyl)-1,3-thiazol-2-yl 109-110                             8 H O 4-(2,4-Dichlorophenyl)-1,3-thiazol-2-yl 136-137                         9 H O 1-Phenyl-1,2,4-triazol-3-yl 88-90                                       10 H O 1-Phenylpyrazol-4-yl 1726,1597,1503,1400,1358,                             1220, 1019                                                                11 H O 1-(4-Fluorophenyl)pyrazol-4-yl 1727,1583,1514,1224,1070,                                               1021                                          12 H O 1-(4-Trifluoromethylphenyl)pyrazol-4-yl 62-84                          13 H O 1-(4-cyanophenyl)pyrazol-4-yl 156-157                                  14 H O 1-(4-Methylphenyl)pyrazol-4-yl 105-107                                 15 H O 1-(4-Chlorophenyl)pyrazol-4-yl 86-90                                   16 H O 1-(2,4-Dichlorophenyl)pyrazol-4-yl 102-104                             17 H O 5-Trifluoromethylisoxazol-3-yl 90-93                                   18 H O 5-Phenylisoxazol-3-yl 95-97                                            19 H O 1-(2,4-Dichlorophenyl)pyrazol-3-yl 121                                 20 H O 1-(4-Chlorophenyl)pyrazol-3-yl 112-113                                 21 H O 1-(3-Chlorophenyl)pyrazol-3-yl 80-84                                   22 H O 1-(4-Fluorophenyl)pyrazol-3-yl 105-107                                 23 H O 1-(4-Methylphenyl)pyrazol-3-yl 110-111                                 24 H S 1-Methylimidazol-2-yl 104-108                                          25 H S 4-Methyl-1,2,4-triazol-3-yl 144                                        26 H O 4-Acetylthiazol-2-yl 110-112                                           27 H O 4-Isopropylthiazol-2-yl 1726,1515,1322,1253,1068                       28 H O 4-Isobutylthiazol-2-yl 1729,1533,1437,1314,1227,                           1069                                                                      29 H O 4-(2-Methylphenyl)thiazol-2-yl 99-100                                  30 H O 4-(3-Methylphenyl)thiazol-2-yl 79-80                                   31 H O 4-(4-Methylphenyl)thiazol-2-yl 121-122                                 32 H O 4-(2-Methoxyphenyl)thiazol-2-yl 111-113                                33 H O 4-(3-Methoxyphenyl)thiazol-2-yl 78-79                                  34 H O 4-(4-Methoxyphenyl)thiazol-2-yl 132-133                                35 H O 4-(3-Bromophenyl)thiazol-2-yl 91-94                                    36 H O 4-(4-Bromophenyl)thiazol-2-yl 123-125                                  37 H O 4-(3-Trifluoromethylphenyl)thiazol-2-yl 85-86                          38 H O 4-(4-Trifluoromethylphenyl)thiazol-2-yl 94-95                          39 H O 2-(4-Fluorophenyl)-5-methylthiazol-4-yl 105-106                        40 H O 5-Cyclopropylisoxazol-3-yl 103-106                                     41 H O 3-(4-Chlorophenyl)-1,2,4-thiadiazol-5-yl 139-140                       42 H O 1-Phenylpyrazol-3-yl 80-83                                             43 H O 5-Methyl-1-phenylpyrazol-4-yl 1726,1598,1503,1361,1188,                    1069                                                                      44 H O 3-(4-Fluorophenyl)-1,2,4-thiadiazol-5-yl 153-155                       45 3-Cl O 1-(4-Chlorophenyl)pyrazol-3-yl 100-104                              46 3-Cl O 1-(4-Methylphenyl)pyrazol-3-yl 141-146                              47 H O 4-(Methoxyiminoethyl)thiazol-2-yl 105-106                              48 H O 4-(Ethoxyiminoethyl)thiazol-2-yl 92-93                                 49 H O 5-(Methoxyiminoethyl)-4-methylthazol-2-yl [sic] 75-76                  50 H O 5-(Ethoxyiminoethyl)-4-methylthiazol-2-yl 95-97                        51 H O 1-(n-Chlorophenyl)-1,2,4-triazol-3-yl 95                               52 H O 1-(4-Chlorophenyl)-5-methyl-1,2,4-triazol-3-yl 1729,1539,1434,135                                 0,1018                                             53 H O 1-Methyl-5-trifluoromethylpyrazol-3-yl 50-52                           54 H O 1-(2-Chlorophenyl)pyrazol-3-yl 85-87                                   55 H O 1-(2,4-Dimethylphenyl)pyrazol-3-yl 95-100                              56 H O 1-(4-Chlorophenyl)-3-methylpyrazol-4-yl 109-114                        57 H O 5-(5-Methyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 128-131                 58 H O 5-(5-Propyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 73-74                   59 H O 5-(5-Hexyl-1,2,4-oxadiazol-3-yl)isoxazol-3-yl 1728,1526,1439,1359                                 ,1221,                                                 1069                                                                      60 H O 1-Methyl-3-phenyl-1,2,4-triazol-5-yl 110                               61 H O 1-(3,5-Dichlorophenyl)-1,2,4-triazol-3-yl 157-160                      62 H O 5-Ethyl-1-phenyl-1,2,4-triazol-3-yl 88-91                              63 H O 1-(2,4-Dichlorophenyl)-1,2,4-triazol-3-yl 129-131                      64 H O 1-(2,6-Dichlorophenyl)pyrazol-3-yl 128-130                             65 3-Cl O 4-(4-Chlorophenyl)-1,3-thiazol-2-yl 154-155                         66 3-Cl O 4-(2,4-Dichlorophenyl)-1,3-thiazol-2-yl 155-158                     67 3-Cl O 1-(2,4-Dichlorophenyl)pyrazol-3-yl 133-135                          68 3-Cl O 1-(4-Chlorophenyl)-1,2,4-triazol-3-yl 130-131                       69 H O 1-(3,4-Dichlorophenyl)pyrazol-3-yl 95-97                               70 H O 1-(2,5-Dichlorophenyl)pyrazol-3-yl 90-93                               71 H O 1-(3,5-Dichlorophenyl)pyrazol-3-yl 130-132                             72 H O 1-(4-Chloro-2-methylphenyl)pyrazol-3-y1 113-155                        73 H O 1-(4-Methoxyphenyl)pyrazol-3-yl 102-105                                74 H O 1-(3-Trifluoromethylphenyl)pyrazol-3-y1 109-111                        75 H O 3-(4-Chlorophenyl)isoxazol-5-yl 113-114                                76 H O 5-Cyanoisoxazol-3-yl 105-107                                           77 H O 5-Methyl-2-(pyrid-2-yl)-1,3-thiazol-4-yl 105-107                       78 H O 5-Methyl-2-(pyrid-3-yl)-1,3-thiazol-4-yl 97-98                         79 H O 5-Methyl-2-(pyrid-4-yl)-1,3-thiazol-4-yl 146-147                       80 H O 5-Methyl-2-(furan-2-yl)-1,3,thiazol-4-yl [sic] 92-93                   81 H O 5-Methyl-2-(thien-2-yl)-1,3-thiazol-4-yl 109-110                       82 H O 5-Methyl-2-(3-methyl- 111-113                                             isoxazol-5-yl)-1,3-thiazol-4-yl                                            83 H O 4-(3-Methylisoxazol-5-yl)-1,3-thiazol-2-yl 98-100                      84 H O 5-Methyl-2-(2-methyl-1,3,thiazol-4-yl)-1,3- 96-97                         thiazol-4-yl [sic]                                                         85 H O 4-(2,4-Dimethyl-1,3-thiazol-5-yl)-1,3-thiazol 117-118                     4-yl                                                                       86 H O 5-Methyl-2-(2-n-heptyl-1,3-thiazol-4-yl)- 73-75                           1,3-thiazol-4-yl                                                           87 H O 4-(2-n-Heptyl-1,3-thiazol-4-yl)-1,3-thiazol- 73-75                        2-yl                                                                       88 H O 5-Methyl-2-phenyl-1,3-thiazol-2-yl 108-110                             89 H O 5-Methoxycarbonylisoxazol-3-yl 77-78                                   90 H O 5-Carbamoylisoxazol-3-yl 142-145                                       91 H O 5-(1,2,4-Oxadiazol-3-yl)isoxazol-3-yl 122-123                          92 H O 4-Methoxycarbonyl-1-phenylpyrazol-3-yl 90-93                           93 H O 1-(2-Methylphenyl)pyrazol-3-yl 81-85                                   94 H O 5-(5-Mercapto-1,3,4-oxadiazol-2-yl)isoxazol- 3348,1730,1556,1478,                                 1368,                                                 3-yl 1071                                                                  95 H O 5-(5-Hydroxy-1,3,4-oxadiazol-2-yl)isoxazol- 3260,1816,1803,1780,1                                 734,                                                  3-yl [sic] 1559,1502,1353,1066                                           __________________________________________________________________________

The compounds I are suitable as fungicides.

The compounds I are distinguished by an outstanding activity against abroad spectrum of phytopathogenic fungi, in particular from the class ofAscomycetes and Basidiomycetes. They are systemically active in somecases and can be employed as foliar and soil fungicides.

They are of particular importance for the control of a multiplicity offungi on various crop plants such as wheat, rye, barley, oats, rice,corn, grass, cotton, soybean, coffee, sugarcane, grapes, fruit anddecorative plants and vegetable plants such as cucumbers, beans andCucurbitaceae, and on the seeds of these plants.

They are specifically suitable for the control of the following plantdiseases:

Erysiphe graminis (powdery mildew) in cereals, Erysiphe cichoracearumand Sphaerotheca fuliginea on Cucurbitaceae, Podosphaera leucotricha onapples, Uncinula necator on vines, Puccinia species on cereals,Rhizoctonia species on cotton and lawns, Ustilago species on cereals andsugarcane, Venturia inaequalis (scab) on apples, Helminthosporiumspecies on cereals, Septoria nodorum on wheat, Botrytis cinerea (graymold) on strawberries, vines, Cercospora arachidicola on groundnuts,Pseudocercosporella herpotrichoides on wheat, barley, Pyricularia oryzaeon rice, Phytophthora infestans on potatoes and tomatoes, Fusarium andVerticillium species on various plants, Plasmopara viticola on vines,Alternaria species on vegetables and fruit.

The compounds I are applied by treating the fungi or the plants, seeds,materials or the soil to be protected from fungal attack with afungicidally effective amount of the active compounds. They are appliedbefore or after the infection of the materials, plants or seeds by thefungi.

They can be converted into the customary formulations, such assolutions, emulsions, suspensions, dusts, powders, pastes and granules.The application form depends on the particular intended use; they shouldin any case guarantee a fine and uniform dispersion of theortho-substituted benzyl ester of a cyclopropanecarboxylic acid. Theformulations are prepared in a known manner, eg. by extending the activecompound with solvents and/or carriers, if desired using emulsifiers anddispersants, it also being possible to use other organic solvents asauxiliary solvent when water is used as a diluent. Suitable auxiliarysubstances for this purpose are essentially: solvents such as aromatics(eg. xylene), chlorinated aromatics (eg. chlorobenzenes), paraffins (eg.mineral oil fractions), alcohols (eg. methanol, butanol), ketones (eg.cyclohexanone), amines (eg. ethanolamine, dimethylformamide) and water;carriers such as ground natural minerals (eg. kaolins, clays, talc,chalk) and ground synthetic minerals (eg. highly disperse silicic acid,silicates); emulsifiers such as nonionic and anionic emulsifiers (eg.polyoxyethylene fatty alcohol ethers, alkylsulfonates andarylsulfonates) and dispersants such as lignin-sulfite waste liquors andmethylcellulose.

The fungicidal compositions in general contain from 0.1 to 95,preferably from 0.5 to 90, % by weight of active compound.

Depending on the type of effect desired, the application rates are from0.02 to 3 kg of active compound per ha.

In seed treatment, active compound amounts of from 0.001 to 50 g,preferably 0.01 to 10 g, per kilogram of seed are in general needed.

The compositions according to the invention can also be present asfungicides together with other active compounds in the application form,the [sic] eg. with herbicides, insecticides, growth regulators,fungicides or alternatively with fertilizers.

On mixing with fungicides, in many cases an enlargement of thefungicidal spectrum of action is obtained here.

The following list of fungicides with which the compounds according tothe invention can be applied together should illustrate the combinationpossibilities, but not restrict it:

sulfur, dithiocarbamtates and their derivatives, such as ferricdimethyldithiocarbamate, zinc dimethyldithiocarbamate, zincethylenebisdithiocarbamate, manganese ethylenebisdithiocarbamate,manganese zinc ethylenediamine bisdithiocarbamate, tetramethylthiuramdisulfide, ammonia complex of zinc (N,N-ethylenebisdithiocarbamate),ammonia complex of zinc (N,N'-propylenebisdithiocarbamate), zinc(N,N'-propylenebisdithiocarbamate),N,N'-polypropylenebis(thiocarbamoyl)disulfide;

nitro derivatives, such as dinitro(1-methylheptyl)phenyl crotonate,2-sec-butyl-4,6-dinitrophenyl 3,3-dimethylacrylate,2-sec-butyl-4,6-dinitrophenyl isopropylcarbonate, diisopropyl5-nitroisophthalate;

heterocyclic substances, such as 2-heptadecyl-2-imidazoline acetate,2,4-dichloro-6-(o-chloroanilino)-s-triazine, O,O-diethylphthalimidophosphonothioate,5-amino-1-[bis(dimethylamino)phosphinyl]-3-phenyl-1,2,4-triazole,2,3-dicyano-1,4-dithioanthraquinone,2-thio-1,3-dithiolo[4,5-b]quinoxaline, methyl1-(butylcarbamoyl)-2-benzimidazole carbamate,2-methoxycarbonylaminobenzimidazole, 2-(fur-2-yl)benzimidazole,2-(thiazol-4-yl)benzimidazole,N-(1,1,2,2-tetrachloroethylthio)tetrahydrophthalimide,N-trichloromethylthiotetrahydrophthalimide,N-trichloromethylthiophthalimide;

N-dichlorofluoromethylthio-N',N'-dimethyl-N-phenylsulfadimide,5-ethoxy-3-trichloromethyl-1,2,3-thiadiazole,2-thiocyanatomethylthiobenzothiazole, 1,4-dichloro-2,5-dimethoxybenzene,4-(2-chlorophenylhydrazono)-3-methyl-5-isoxazolone,2-thiopyridine-1-oxide, 8-hydroxyquinoline or its copper salt,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin,2,3-dihydro-5-carboxanilido-6-methyl-1,4-oxathiin-4,4-dioxide,2-methyl-5,6-dihydro-4H-pyran-3-carboxanilide,2-methylfuran-3-carboxanilide, 2,5-dimethylfuran-3-carboxanilide,2,4,5-trimethylfuran-3-carboxanilide,N-cyclohexyl-2,5-dimethylfuran-3-carboxamide,N-cyclohexyl-N-methoxy-2,5-dimethylfuran-3-carboxamide,2-methylbenzanilide, 2-iodobenzanilide,N-formyl-N-morpholine-2,2,2-trichloroethyl acetal,piperazine-1,4-diylbis(1-(2,2,2-trichloroethyl)formamide [sic],1-(3,4-dichloroanilino)-1-formylamino-2,2,2-trichloroethane,2,6-dimethyl-N-tridecylmorpholine or its salts,2,6-dimethyl-N-cyclododecylmorpholine or its salts,N-[3-(p-tert-butylphenyl)-2-methylpropyl]-cis-2,6-dimethylmorpholine,N-[3-(p-tert-butylphenyl)-2-methylpropyl]piperidine,1-[2-(2,4-dichlorophenyl)-4-ethyl-1,3-dioxolan-2-yl-ethyl]-1H-1,2,4-triazole,1-[2-(2,4-dichlorophenyl)-4-n-propyl-1,3-dioxolan-2-ylethyl]-1H-1,2,4-triazole,N-(n-propyl)-N-(2,4,6-trichlorophenoxyethyl)-N'-imidazolylurea,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanone,1-(4-chlorophenoxy)-3,3-dimethyl-1-(1H-1,2,4-triazol-1-yl)-2-butanol,α-(2-chlorophenyl)-α-(4-chlorophenyl)-5-pyrimidinemethanol,5-butyl-2-dimethylamino-4-hydroxy-6-methylpyrimidine,bis(p-chlorophenyl)-3-pyridinemethanol,1,2-bis(3-ethoxycarbonyl-2-thioureido)benzene,1,2-bis(3-methoxycarbonyl-2-thioureido)benzene, and also variousfungicides, such as dodecylguanidine acetate,3-[3-(3,5-dimethyl-2-oxycyclohexyl)-2-hydroxyethyl]glutarimide,hexachlorobenzene, DL-methyl-N-(2,6-dimethylphenyl)-N-2-furoylalaninate, DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)alanine methylester, N-(2,6-dimethylphenyl)-N-chloroacetyl-D,L-2-aminobutyrolactone,DL-N-(2,6-dimethylphenyl)-N-(phenylacetyl)alanine methyl ester,5-methyl-5-vinyl-3-(3,5-dichlorophenyl)-2,4-dioxo-1,3-oxazolidine,3-[3,5-dichlorophenyl(-5-methyl-5-methoxymethyl]-1,3-oxazolidine-2,4-dione[sic], 3-(3,5-dichlorophenyl)-1-isopropylcarbamoylhydantoin,N-(3,5-dichlorophenyl)-1,2-dimethylcyclopropane-1,2-dicarboximide,2-cyano-[N-ethylaminocarbonyl-2-methoximino]acetamide,1-[2-(2,4-dichlorophenyl)pentyl]-1H-1,2,4-triazole,2,4-difluoro-α-(1H-1,2,4-triazolyl-1-methyl)benzhydryl alcohol,N-(3-chloro-2,6-dinitro-4-trifluoromethylphenyl)-5-trifluoromethyl-3-chloro-2-aminopyridine,1-((bis (4-fluorophenyl)methylsilyl)methyl)-1H-1,2,4-triazole.

The following active compounds are particularly preferred as mixturecomponents:

1-(2-cyano-2-methoxyiminoacetyl)-3-ethylurea (common name: cymoxanil,U.S. Pat. No. 3,957,847); manganese ethylenebis(dithiocarbamate zinccomplex) (common name: mancozeb, U.S. Pat. No. 3,379,610); manganeseethylenebis(dithiocarbamate) (common name: maneb, U.S. Pat. No.2,504,404); zinc ammoniate ethylenebis(dithiocarbamate) (former commonname: metiram, U.S. Pat. No. 3,248,400); zincethylenebis(dithiocarbamate) (common name: zineb, U.S. Pat. No.2,457,674),(^(#))-cis-4-[3-(4-tert-butylphenyl)-2-methylpropyl]-2,6-dimethylmorpholine[sic] (common name: fenpropimorph, U.S. Pat. No. 4,202,894);(RS)-1-[3-(4-tert-butylphenyl)-2-methylpropyl]piperidine (common name:fenpropidin, U.S. Pat. No. 4,202,894); 2,6-dimethyl-4-[C₁₁ -C₁₄-alkyl]morpholine (common name: tridemorph, DE-A 11 64 152);1-[(2RS,4RS;2RS,4SR)-4-bromo-2-(2,4-dichlorophenyl)tetrahydrofuryl]-1H-1,2,4-triazole[common name: bromuconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 5-6,(1990) 439];2-(4-chlorophenyl)-3-cyclopropyl-1-(1H-1,2,4-triazol-1-yl)butan-2-ol(common name: cyproconazole, U.S. Pat. No. 4,664,696);(^(#))-4-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-2-yl]phenyl[sic] 4-chlorophenyl ether (common name: difenoconazole, GB-A2,098,607);(E)-(R,S)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)pent-1-en-3-ol(common name: diniconazole, CAS RN [83657-24-3]);(Z)-2-(1H-1,2,4-triazol-1-ylmethyl)-2-(4-fluorophenyl)-3-(2-chlorophenyl)oxirane(common name: epoxyconazole, EP-A 196 038);4-(4-chlorophenyl)-2-phenyl-2-(1H-1,2,4-triazolylmethyl)butyronitrile(common name: fenbuconazole (proposed), EP-A 251 775);3-(2,4-dichlorophenyl)-6-fluoro-2-(1H-1,2,4-triazol-1-yl)quinazolin-4(3H)one[common name: fluquinconazole, Proc. Br. Crop Prot. Conf. Pests Dis.,5-3, (1992) 411]; bis(4-fluorophenyl)(methyl)(1H-1,2,4-triazol-1-ylmethyl)silane [common name: flusilazole, Proc. Br.Crop Prot. Conf. Pests Dis., 1, (1984) 413];(R,S)-2-(2,4-dichlorophenyl)-1-(1H-1,2,4-triazol-1-yl)hexan-2-ol (commonname: hexaconazole, CAS RN [79983-71-4]);(1RS,5RS;1RS,5SR)-5-(4-chlorobenzyl)-2,2-dimenthyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol[common name: metconazole, Proc. Br. Crop Prot. Conf. Pests Dis., 5-4,(1992) 419];N-propyl-N-[2-(2,4,6-trichlorophenoxy)ethyl]imidazole-1-carboxamide(common name: prochloraz, U.S. Pat. No. 3,991,071);(±)-1-[2-(2,4-dichlorophenyl)-4-propyl-1,3-dioxolan-2-ylmethyl]-1H-1,2,4-triazole(common name: propiconazole, GB-A 1,522,657);(R,S)-1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol(common name: tebuconazole, U.S. Pat. No. 4,723,984);(±)-2-(2,4-dichlorophenyl)-3-(1H-1,2,4-triazol-1-yl)propyl1,1,2,2-tetrafluoroethyl ether [common name: tetraconazole, Proc. Br.Crop Prot. Conf. Pests Dis., 1, (1988) 49];(E)-1-[1-[[4-chloro-2-(trifluoromethyl)phenyl]imino]-2-propoxyethyl]-1H-imidazole(common name: triflumizole, JP-A 79/119,462);(RS)-2,4'-difluoro-alpha-(1H-1,2,4-triazol-1-ylmethyl)benzhydryl alcohol(common name: flutriafol, CAS RN [76674-21-0];1-[2-(2,5-dimethylphenoxymethyl)phenyl)-1-methoxyimino-N-methylacetamide(EP-A 477 631); methyl1-[2-(2-methylphenoxymethyl)phenyl]-1-methoxyiminoacetate (EP-A 253213); methyl1-{2-[6-(3-cyanophenoxy)pyrimidin-4-yloxy]phenyl}-1-methoxyiminoacetate(EP-A 382 375); N-(trichloromethylthio)cyclohex-4-ene-1,2-dicarbimide(common name: captan, U.S. Pat. No. 2,553,770);N-(trichloromethylthio)phthalimide (common name: folpet, U.S. Pat. No.2,553,770); 4,6-dimethyl-2-phenylaminopyrimidine (common name:pyrimethanil, DD-A 151 404); 4-methyl-2-phenylamino-6-propynylpyrimidine(common name: mepanipyrim, EP-A 224 339);4-cyclopropyl-6-methyl-2-phenylaminopyrimidine (EP-A 310 550).

The compounds of the formula I are additionally suitable to controlpests from the class of insects, arachnida and nematodes effectively.They can be employed as pesticides in plant protection and in thehygiene, stored products protection and veterinary sector.

The harmful insects include from the order of the butterflies(Lepidoptera), for example, Agrotis ypsilon, Agrotis segetum, Alabamaargillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographagamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana,Cheimatobia brumata, Choristoneura fumiferana, Choristoneuraoccidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini,Diaphania nitidalis, Diatraea grndiosella [sic], Earias insulana,Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana,Feltia subterranea, Galleria mellonella, Grapholita funebrana,Grapholita molesta, Heliothis armigera, Heliothis virescens, Heliothiszea, Hellula undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeutamalinellus, Keifferia lycopersicella, Lambdina fiscellaria, Laphygmaexigua, Leucoptera coffeella, Leucoptera scitella, Lithocolletisblancardella, Lobesia botrana, Loxostege sticticalis, Lymantria dispar,Lymantria monacha, Lyonetia clerkella, Malacosoma neustria, Mamestrabrassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flamea,Petcinophora gossypiella, Peridroma saucia, Phalera bucephala,Phthorimaea operculella, Phyllocnistis citrella, Pieris brassicae,Plathypena scarbra, Plutella xylostella, Pseudoplusia includens,Phyacionia frustrana, Scrobipalpula absoluta, Sitotroga cerelella,Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis,Spodoptera litura, Thaumatopoea pityocampa, Tortrix viridana,Trichoplusia ni, Zeiraphera canadensis.

From the order of the beetles (Coleoptera), for example, Agrilussinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallussolstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum,Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchusrufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassidanebulosa, Cerotoma trifurcata, Ceuthorrhynchus assimilis, Ceuthorrynchusnapi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi,Diabrotica longicornis, Diabrotica 12-punctata, Diabrotica virgifera,Epilachna varivestis, Epitrix hirtipennis, Eutinobothrus brasiliensis,Hylobius abietis, Hypera brunneipennis, Hypera postica, Ips typographus,Lema bilineata, Lema melanopus, Leptinotarsa decemlineata, Limoniuscalifornicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethesaeneus, Melolontha hippocastani, Melolontha melolontha, Onlema oryzae,Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae,Phyllotetra chrysocephala, Phyllophaga sp., Phyllopertha horticola,Phyllotetra nemorum, Phyllotetra striolata, Popilla japonica, Sitonalineatus, Sitophilus granaria.

From the order of the dipterous insects (Diptera), for example, Aedesaegypti, Aedes vexans, Anastrepha ludens, Anopheles maculipennis,Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomyamacellaria, Contarinia sorghicola, Cordylobia anthropophaga, Culexpipiens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Fanniacanicularis, Gasterophilus intestinalis, Glossia morsitans, Haematobiairritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata,Liriomyza sativae, Liriomyza trifolii, Lucila caprina, Lucilia cuprina,Lucilia sericata, Lycoria pectoralis, Mayetiola destructor, Muscadomestica, Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomyahysocyami, Phorbia antiqua, Phorbia brassicae, Phorbia coarctata,Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipulaoleracea, Tipula paludosa.

From the order of the thrips (Thysanoptera), for example, Frankliniellafusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothripscitri, Thrips oryzae, Thrips palmi, Thrips tabaci.

From the order of the hymenopterous insects (Hymenoptera), for example,Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampaminuta, Hoplocampa testudinea, Monomorium pharaonis, Solenopsisgeminata, Solenopsis invicta.

From the order of the bed bugs (Heteroptera), for example, Acrosternumhilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus,Dysdercus intermedius, Eurygaster integriceps, Euchistus impictiventris,Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezaraviridula, Piesma quadrata, Solubea insularis, Thyanta perditor.

From the order of the plant-sucking insects (Homoptera), for example,Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphisfabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicorynebrassicae, Cerosipha gossypii, Dreyfusia nordmannianae, Dreyfusiapiceae, Dyasphis radicola, Dysaulacorthum pseudosolani, Empoasca fabae,Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphon rosae, Megouraviciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi,Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida,Phorodon humuli, Psylla mali, Psylla piri, Rhopalomyzus ascalonicus,Rhopalosiphum maidis, Sappaphis mala, Sappaphis mali, Schizaphisgraminum, Schizoneura lanuginosa, Trialeurodes vaporariorum, Viteusvitifolii.

From the order of the termites (Isoptera), for example, Calotermesflavicollis, Leucotermes flavipes, Reticulitermes lucifugus, Termesnatalensis.

From the order of the orthopterous insects (Orthoptera), for example,Acheta domestica, Blatta orientalis, Blattella germanica, Forficulaauricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplusbirittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplussanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Periplanetaamericana, Schistocerca americana, Schistocerca peregrina, Stauronotusmaroccanus, Tachycines asynamorus.

From the class of the Arachnoidea, for example spiders (Acarina) such asAmblyomma americanum, Amblyomma variegatum, Argas persicus, Boophilusannulatus, Boophilus decoloratus, Boophilus microplus, Brevipalpusphoenicis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychuscarpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodesrubicundus, Ornithodorus moubata, Otobins megnini, Paratetranychuspilosus, Permanyssus gallinae, Phyllocaptrata oleivora,Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus,Rhipicephalus evertsi, Saccoptes scabiei, Tetranychus cinnabarinus,Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius,Tetranychus urticae.

From the class of the nematodes, for example, root gall nematodes, eg.Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica,cyst-forming nematodes, eg. Globodera rostochiensis, Heterodera avenae,Heterodera glycinae, Heterodera schatii, Heterodera trifolii, stem andleaf eelworms, eg. Belonolaimus longicaudatus, Ditylenchus destructor,Ditylenchus dipsaci, Heliocotylenchus multicinctus, Longidoruselongatus, Radopholus similis, Rotylenchus robustus, Trichodorusprimitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius,Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus curvitatus,Pratylenchus goodeyi.

The active compounds can be applied as such or in the form of theirformulations or the application forms prepared therefrom, eg. in theform of directly sprayable solutions, powders, suspensions ordispersions, emulsions, oil dispersions, pastes, dusts, scatteringcompositions or granules by spraying, atomizing, dusting, scattering orpouring. The application forms depend entirely on the purposes of use;they should in any case as far as possible guarantee the finestdispersion of the active compounds according to the invention.

The active compound concentrations in the ready-for-applicationpreparations can be varied within substantial ranges.

In general, they are from 0.0001 to 10%, preferably from 0.01 to 1%.

The active compounds can also be used with success in ultra-low volumeprocesses (ULV), where it is possible to apply formulations containingmore than 95% by weight of active compound or even the active compoundwithout additives.

The application rates of active compound for controlling pests underoutdoor conditions is from 0.1 to 2.0, preferably from 0.2 to 1.0 kg/ha.

For the preparation of directly sprayable solutions, emulsions, pastesor oil dispersions, mineral oil fractions of medium to high boilingpoints, such as kerosene or diesel oil, and also coal tar oils and oilsof vegetable or animal origin, aliphatic, cyclic and aromatichydrocarbons, eg. benzene, toluene, xylene, paraffin,tetrahydronaphthalene, alkylated naphthalenes or their derivatives,methanol, ethanol, propanol, butanol, chloroform, carbon tetrachloride,cyclohexanol, cyclohexanone, chlorobenzene, isophorone, strongly polarsolvents, eg. dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidoneand water are suitable.

Aqueous application forms can be prepared from emulsion concentrates,pastes or wettable powders (oil dispersions) by addition of water. Forthe preparation of emulsions, pastes or oil dispersions, the substancescan be homogenized in water as such or dissolved in an oil or solvent,by means of wetting agents, tackifiers, dispersants or emulsifiers.However, the concentrates consisting of active substance, wetting agent,tackifier, dispersant or emulsifier and possibly solvent or oil can alsobe prepared, which are suitable for dilution with water.

Suitable surface-active substances are alkali metal, alkaline earthmetal and ammonium salts of lignosulfonic acid, naphthalenesulfonicacid, phenolsulfonic acid, dibutylnaphthalenesulfonic acid,alkylarylsulfonates, alkylsulfates, alkylsulfonates, fatty alcoholsulfates and fatty acids and their alkali metal and alkaline earth metalsalts, salts of sulfated fatty alcohol glycol ethers, condensationproducts of sulfonated naphthalene and naphthalene derivatives withformaldehyde, condensation products of naphthalene or ofnaphthalenesulfonic acid with phenol and formaldehyde, polyoxyethyleneoctylphenol [sic] ether, ethoxylated isooctylphenol, octylphenol,nonylphenol, alkylphenol [sic] polyglycol ether, tributylphenylpolyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol,fatty alcohol ethylene oxide condensates, ethoxylated castor oil,polyoxyethylene alkyl ethers, ethoxylated polyoxypropylene, laurylalcohol polyglycol ether acetal, sorbitol esters, lignin-sulfite wasteliquors and methylcellulose.

Powders, scattering compositions and dusts can be prepared by mixing orjoint grinding of the active substances with a solid carrier.

The formulations in general contain from 0.01 to 95% by weight,preferably from 0.1 to 90% by weight, of the active compound. The activecompounds are employed here in a purity of from 90% to 100%, preferably95% to 100% (according to NMR spectrum).

Examples of formulations are:

I. 5 parts by weight of the compound No. 1 from Table B are intimatelymixed with 95 parts by weight of finely divided kaolin. A dust whichcontains 5% by weight of the active compound is obtained in this way.

II. 30 parts by weight of the compound No. 2 from Table B are intimatelymixed with a mixture of 92 parts by weight of powdered silica gel and 8parts by weight of paraffin oil which has been sprayed on the surface ofthis silica gel. A preparation of the active compound having goodadhesion is obtained in this way (active compound content 23% byweight).

III. 10 parts by weight of the compound No. 3 from Table B are dissolvedin a mixture which consists of 90 parts by weight of xylene, 6 parts byweight of the addition product of 8 to 10 mol of ethylene oxide to 1 molof oleic acid N-monoethanolamide, 2 parts by weight of calcium salt ofdodecylbenzenesulfonic acid and 2 parts by weight of the additionproduct of 40 mol of ethylene oxide to 1 mol of castor oil (activecompound content 9% by weight).

IV. 20 parts by weight of the compound No. 4 from Table B are dissolvedin a mixture which consists of 60 parts by weight of cyclohexanone, 30parts by weight of isobutanol, 5 parts by weight of the addition productof 7 mol of ethylene oxide to 1 mol of isooctylphenol and 5 parts byweight of the addition product of 40 mol of ethylene oxide to 1 mol ofcastor oil (active compound content 16% by weight).

V. 80 parts by weight of the compound No. 5 from Table B are well mixedwith 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-alpha-sulfonic acid, 10 parts by weight of thesodium salt of a lignosulfonic acid from a sulfite waste liquor and 7parts by weight of powdered silica gel and the mixture is ground in ahammer mill (active compound content 80% by weight).

VI. 90 parts by weight of the compound No. 6 from Table B are mixed with10 parts by weight of N-methyl-α-pyrrolidone and a solution is obtainedwhich is suitable for application in the form of very small drops(active compound content 90% by weight).

VII. 20 parts by weight of the compound No. 7 from Table B are dissolvedin a mixture which consists of 40 parts by weight of cyclohexanone, 30parts by weight of isobutanol, 20 parts by weight of the additionproduct of 7 mol of ethylene oxide to 1 mol of isooctylphenol and 10parts by weight of the addition product of 40 mol of ethylene oxide to 1mol of castor oil. By pouring the solution into and finely dispersing itin 100,000 parts by weight of water, an aqueous dispersion is obtainedwhich contains 0.02% by weight of the active compound.

VIII. 20 parts by weight of the active compound No. 8 from Table B arewell mixed with 3 parts by weight of the sodium salt ofdiisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodiumsalt of a lignosulfonic acid from a sulfite waste liquor and 60 parts byweight of powdered silica gel and the mixture is ground in a hammermill. By finely dispersing the mixture in 20,000 parts by weight ofwater, a spray liquor is obtained which contains 0.1% by weight of theactive compound.

Granules, eg. coated, impregnated and homogeneous granules, can beproduced by binding the active compounds to solid carriers. Solidcarriers are eg. mineral earths, such as silica gel, silicic acids,silica gels (sic], silicates, talc, kaolin, attapulgite, limestone,lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calciumsulfate and magnesium sulfate, magnesium oxide, ground syntheticmaterials, fertilizers, such as eg. ammonium sulfate, ammoniumphosphate, ammonium nitrate, ureas and vegetable products, such as grainmeal, tree bark, wood and nut shell meal, cellulose powder and othersolid carriers.

Oils of various types, herbicides, fungicides, other pesticides andbactericides can be added to the active compounds, if appropriate alsojust immediately before application (tank mix). These agents can beadmixed to the compositions according to the invention in the weightratio 1:10-10:1.

Application Examples

1. Fungicidal Activity

It was possible to show the fungicidal action of the compounds of thegeneral formula I by the following tests:

The active compounds were prepared as a 20% strength emulsion in amixture of 70% by weight of cyclohexanol, 20% by weight of Nekanil® LN(Lutensol® AP6, wetting agent with emulsifier and dispersant actionbased on ethoxylated alkylphenols) and 10% by weight of Emulphor® EL(Emulan® EL, emulsifier based on ethoxylated fatty alcohols) andaccordingly diluted to the desired concentration with water.

1.A Erysiphe graminis var. tritici (Wheat Mildew)

Wheat seedlings of the variety Fruhgold were sprayed with an aqueousactive compound suspension until dripping wet. After 24 h, the plantswere dusted with oidia (spores) of the fungus Erysiphe graminis var.tritici (wheat mildew). After 7 days at 22° C.-24° C. and 75-80%atmospheric humidity, the fungal infestation of the leaves was assessed.

In this test, the plants treated with 63 ppm of the compounds 3, 7, 8,9, 11, 12, 14, 18, 19, 23, 27, 32, 33, 35, 49, 50, 51, 53, 54, 55, 56,57, 58 and 59 showed an infestation of 15% and less, while in theuntreated plants 65% of the leaf surfaces were infested.

1.B Plasmopara viticola (Vine Peronospora)

Potted vines of the variety Muller-Thurgau were sprayed with an aqueousactive compound suspension until dripping wet. After 8 days in thegreenhouse, the leaves were infected with a zoospore suspension ofPlasmopara viticola (vine Peronospora). The plants were first placed for48 hours at 24° C. in a water vapor-saturated chamber, then for 5 daysin the greenhouse at 20° C.-30° C. and subsequently for a further 16hours at 24° C. in a water vapor-saturated chamber before theinfestation was assessed.

In this test, the plants treated with 63 ppm of the compounds 3, 7, 8,9, 10, 11, 12, 14, 15, 16, 17, 18, 21, 22, 23, 24, 25, 26, 27, 33, 34,35, 36, 37, 38, 39, 40, 41, 42, 23 [sic], 44 and 48 showed aninfestation of 15% and less, while in the untreated plants 80% of theleaf undersides were infested.

1.C Pyricularia oryzae (Protective Action)

Leaves of rice seedlings of the variety Tai-Nong 67 were sprayed withaqueous emulsions of the active compounds (content of dry matter: 80%active compound and 20% emulsifier) until dripping wet and inoculated 24hours later with a spore suspension of Pyricularia oryzae. The testplants were then stored in climatic chambers at 22-24 ° C. and 95-99%relative atmospheric humidity. After 6 days, the extent of theinfestation was determined.

In this test, the plants treated with 250 ppm of the compounds 3, 7, 8,10, 11, 12, 20, 21, 22, 23, 24, 25, 26, 27, 32, 33, 38, 48, 49, 50, 51,52, 53, 54 and 55 showed an infestation of 15% and less, while in theuntreated plants 70% of the leaf surfaces were infested.

2. Action Against Animal Pests

It was possible to show the insecticidal action of the compounds of thegeneral formula I by the following tests:

The Active Compounds Were Prepared

a) as a 0.1% strength solution in acetone or

b) as a 10% strength emulsion in a mixture of 70% by weight ofcyclohexanone, 20% by weight of Nekanil® LN (Lutensol® AP6, wettingagent with emulsifier and dispersant action based on ethoxylatedalkylphenols) and 10% by weight of Emulphor® EL (Emulan® EL, emulsifierbased on ethoxylated fatty alcohols)

and diluted with acetone in the case of a) or with water in the case ofb) according to the desired concentration.

After conclusion of the tests, the lowest concentration in each case wasdetermined at which the compounds still caused a 80-100% inhibition ormortality in comparison to untreated control tests (activity thresholdor minimum concentration respectively).

2.A Aphis fabae (Blackfly), Contact Action

Heavily infested bush beans (Vicia faba) were treated with the aqueousactive compound preparation.

The mortality rate was determined after 24 h.

In this test, the compounds 9, 18, 24, 37, 42, 43 and 44 showed activitythresholds of at least 400 ppm.

2.B Nephotettix cincticeps (Green Rice Cicada), Contact Action

Round filters were treated with the aqueous active compound preparationand then subjected to occupation by 5 adult cicadas.

The mortality was assessed after 24 h.

In this test, the compounds 3, 16, 24, 32, 33, 36, 40, 42, 46, 50, 51,55, 56, 58, 61 and 63 showed activity thresholds of at least 0.4 mg.

2.C Prodenia litura (Egyptian Cotton Leafworm), Growth Test

Five caterpillars of the development stage L3 (10-12 mm) which hadsuffered no ascertainable damage in the contact test were applied tostandard nutrient medium (3.1 l of water, 80 g of agar, 137 g ofbrewer's yeast, 515 g of corn meal, 130 g of wheatgerm and customaryadditives and vitamins (20 g of Wesson salt, 5 g of Nipagin, 5 g ofSorbin, 10 g of cellulose, 18 g of ascorbic acid, 1 g of Lutavit® blend(vitamin), 5 ml of alcoholic biotin solution), which had previously beenwetted with the aqueous active compound preparation. The observationextended until hatching of the moths in a control test without activecompound.

In this test, the compounds 9, 24, 26, 40, 42, 43, 44, 51, 52 and 63showed activity thresholds of at least 0.4 mg.

2.D Tetranychus telarius (Red Spider Mite), Contact Action

Heavily infested potted bush beans which had the second pair of adultleaves were treated with aqueous active compound preparation.

After 5 days in the greenhouse, the success of the control wasdetermined by means of a binocular microscope.

In this test, the compounds 7, 8, 9, 18, 23, 24, 37, 40, 42, 23 [sic],44, 49, 50, 51, 52, 61 and 63 showed activity thresholds of at least 400ppm.

We claim:
 1. A compound of the formula I ##STR21## wheren is 0; X is 0;Y is 3-pyrazolyl; and R² 4-chlorophenyl.
 2. A compound of the formula I##STR22## where the index and the substituents have the followingmeanings R² is phenyl, Y is pyrazole, X is O or S, and n is
 0. 3. Acompound of the formula I ##STR23## where the index and the substituentshave the following meanings wherein R² is phenyl Y is pyrazole, X is Oand n is 0.